[ CAS No. 434-75-3 ] {[proInfo.proName]}

Name: 434-75-3|2-Chloro-6-fluorobenzoic acid|98%
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Quality Control of [ 434-75-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 434-75-3 ]

CAS No. :	434-75-3	MDL No. :	MFCD00002417
Formula :	C₇H₄ClFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XNTIGDVFBDJLTQ-UHFFFAOYSA-N
M.W :	174.56	Pubchem ID :	67947
Synonyms :

Calculated chemistry of [ 434-75-3 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.37
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.29
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	2.6
Log Po/w (MLOGP) :	2.63
Log Po/w (SILICOS-IT) :	2.28
Consensus Log Po/w :	2.18

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.59
Solubility :	0.45 mg/ml ; 0.00258 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.522 mg/ml ; 0.00299 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.66
Solubility :	0.379 mg/ml ; 0.00217 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.4

Safety of [ 434-75-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 434-75-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 434-75-3 ]
Downstream synthetic route of [ 434-75-3 ]

[ 434-75-3 ] Synthesis Path-Upstream 1~8

1
[ 387-45-1 ]
[ 434-75-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 3 h;	To the solution of 2-chloro-6-fluorobenzaidehyde {1 ,0 g, 6.31 mmoi) in 25 mL of THF and 10 ml of H2O was added 8H2PO4 (454 rng, 3.78 mmoi). The reaction was stirred 10 min at room temperature before introduction of NaCiC (1.88 g, 20.8_.1 mmoi) and 1 ,4 mL of H₂O₂ (30percentwt ._.in H2O), The reaction was stirred at room temperature 3h, Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were washed with an aqueous solution of NaOH 1 .. The combined aqueous layers were acidified to pH-1 ^'with an aqueous solution of HG 1 and wer extracted with EtOAc. The combined organic layers were washed with brine and dried over >SQ . Filtration and removal of the solven in. vacuo provided 1.10 g (99percent) of the title compound as a colorless solid which was used without further purification; ^{FontWeight="Bold" FontSize="10"}H NMR (400 MHz, CDC ) δ - 7.44 - 7.37 (m, 1 H), 7.31 - 7.27 (m, 1 H), 7.1 - 7,07 (m, 1 H},

Reference： [1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1, . Location in patent: Page/Page column 47-48
[3] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970
[4] Chemische Berichte, 1936, vol. 69, p. 2253,2255
[5] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970

2
[ 668-45-1 ]
[ 434-75-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	at 60 - 65℃; for 2.5 h; Green chemistry	General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO₄ and the reaction mixture was heated at 60-65 °C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90percent) in all cases. All final products obtained were found sufficiently pure so it didn’t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95percent ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 28, p. 3802 - 3804

3
[ 443-33-4 ]
[ 434-75-3 ]

Reference： [1] Synthetic Communications, 2001, vol. 31, # 20, p. 3151 - 3159

4
[ 443-83-4 ]
[ 434-75-3 ]

Reference： [1] Journal of the Indian Chemical Society, 1944, vol. 21, p. 112,114
[2] Chemical and Pharmaceutical Bulletin, 1979, vol. 27, # 6, p. 1287 - 1298
[3] Chemische Berichte, 1936, vol. 69, p. 2253,2255

5
[ 124-38-9 ]
[ 625-98-9 ]
[ 434-75-3 ]

Reference： [1] Tetrahedron Letters, 1996, vol. 37, # 36, p. 6551 - 6554

6
[ 95-52-3 ]
[ 434-75-3 ]

Reference： [1] Journal of the Indian Chemical Society, 1944, vol. 21, p. 112,114

7
[ 434-75-3 ]
[ 363-51-9 ]

Reference： [1] Journal of Organic Chemistry, 1955, vol. 20, p. 1577,1589
[2] Patent: US4032639, 1977, A,

8
[ 434-75-3 ]
[ 56961-31-0 ]

Reference： [1] Dalton Transactions, 2018, vol. 47, # 12, p. 4341 - 4351

[ 434-75-3 ] Synthesis Path-Downstream 1~88

1
[ 443-83-4 ]
[ 434-75-3 ]

Reference： [1]Journal of the Indian Chemical Society,1944,vol. 21,p. 112,114
[2]Chemical and Pharmaceutical Bulletin,1979,vol. 27,p. 1287 - 1298
[3]Chemische Berichte,1936,vol. 69,p. 2253,2255

2
[ 387-45-1 ]
[ 434-75-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In tetrahydrofuran; water; at 20℃; for 3h;	To the solution of 2-chloro-6-fluorobenzaidehyde {1 ,0 g, 6.31 mmoi) in 25 mL of THF and 10 ml of H2O was added 8H2PO4 (454 rng, 3.78 mmoi). The reaction was stirred 10 min at room temperature before introduction of NaCiC (1.88 g, 20.8.1 mmoi) and 1 ,4 mL of H2O2 (30%wt ..in H2O), The reaction was stirred at room temperature 3h, Upon completion, the reaction mixture was extracted with EtOAc. The combined organic layers were washed with an aqueous solution of NaOH 1 .. The combined aqueous layers were acidified to pH-1 'with an aqueous solution of HG 1 and wer extracted with EtOAc. The combined organic layers were washed with brine and dried over >SQ . Filtration and removal of the solven in. vacuo provided 1.10 g (99%) of the title compound as a colorless solid which was used without further purification; FontWeight="Bold" FontSize="10" H NMR (400 MHz, CDC ) delta - 7.44 - 7.37 (m, 1 H), 7.31 - 7.27 (m, 1 H), 7.1 - 7,07 (m, 1 H},

Reference： [1]ChemMedChem,2016,vol. 11,p. 2607 - 2620
[2]Patent: WO2018/52903,2018,A1 .Location in patent: Page/Page column 47-48
[3]Tetrahedron Letters,1988,vol. 29,p. 1967 - 1970
[4]Chemische Berichte,1936,vol. 69,p. 2253,2255
[5]Tetrahedron Letters,1988,vol. 29,p. 1967 - 1970

3
[ 90-05-1 ]
[ 434-75-3 ]
[ 57317-67-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2357 - 2362

4
[ 959992-18-8 ]
[ 434-75-3 ]
C₂₆H₂₅ClFN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 20℃; for 30h;	Example 28.1; N-(2-chloro-6-fluorobenzovn-0-[2-(3,4-dihvdro-2H-pyrido[3.2-bU1.41oxazin-6- vDethvU -L-tyrosine; To a solution of 2-chloro-5-fluorobenzoic acid (65 mg, 0.37 mmol) in DMF (1 ml) were added TBTU (141 mg, 0.37 mmol) and methyl O-[2-(3,4-dihydro-2H-pyrido[3,2- b][l,4]oxazin-6-yl)ethyl]-L-tyrosinate (120 mg, 0.34 mmol). The mixture was stirred at room temperature for 30 hours. LiOH (62 mg, 1.34 mol) and H2O (0.2 ml) were then added. After stirring for 12 hours, the resulting mixture was purified by Cl 8 reverse phase chromatography (basic conditions) to give the title compound (125 mg, 74%); Mass Spectrum [M+H]+ = 500; 1H NMR Spectrum: (DMSO-d6) 2.87 (t, 2H), 2.89 (dd, IH), 3.06 (dd, IH), 3.34-3.38 (m, 2H), 4.07 (t, 2H), 4.17 (t, 2H), 4.41 (dd, IH), 6.41 (d, IH), 6.65

Reference： [1]Patent: WO2007/141473,2007,A1 .Location in patent: Page/Page column 245-246

5
[ 137-07-5 ]
[ 434-75-3 ]
2-(2-chloro-6-fluorophenyl)benzo[d]thiazole [ No CAS ]

Reference： [1]Magnetic Resonance in Chemistry,2006,vol. 44,p. 102 - 105

6
[ 696-62-8 ]
[ 434-75-3 ]
2-chloro-6-fluoro-4'-methoxybiphenyl [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1781 - 1783
[2]Tetrahedron,2009,vol. 65,p. 4635 - 4638

7
[ 96-50-4 ]
[ 434-75-3 ]
6-fluoro-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1853 - 1864
[2]Magnetic Resonance in Chemistry,2009,vol. 47,p. 174 - 178

8
[ 7305-71-7 ]
[ 434-75-3 ]
6-fluoro-2-methyl-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 1853 - 1864
[2]Magnetic Resonance in Chemistry,2009,vol. 47,p. 174 - 178

9
[ 434-75-3 ]
benzoic acid N'-tert-butyl-N'-(2-chloro-6-fluoro-benzoyl)-hydrazide [ No CAS ]

Reference： [1]Pesticide Science,1994,vol. 41,p. 139 - 148

10
[ 434-75-3 ]
[ 213208-10-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 675 - 686

11
[ 434-75-3 ]
5-{2-[4-(4-Diethylamino-butyl)-phenyl]-acetyl}-1-fluoro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 675 - 686

12
[ 434-75-3 ]
5-{2-[4-(4-Diisopropylamino-butyl)-phenyl]-acetyl}-1-fluoro-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 675 - 686

13
[ 434-75-3 ]
[ 57317-25-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2357 - 2362

14
[ 434-75-3 ]
[ 57317-80-3 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2357 - 2362

15
[ 434-75-3 ]
[ 57317-73-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2357 - 2362

16
[ 95-52-3 ]
[ 434-75-3 ]

Reference： [1]Journal of the Indian Chemical Society,1944,vol. 21,p. 112,114

17
[ 544704-12-3 ]
[ 434-75-3 ]
C₂₇H₃₂ClF₄N₃O [ No CAS ]

Reference： [1]Patent: US6391865,2002,B1 .Location in patent: Page column 38

18
[ 554418-82-5 ]
[ 434-75-3 ]
[ 554418-86-9 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 30℃; for 24h;	1-hydroxybenzotriazol monohydrate (37 mg), <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (42 mg), triethylamine (34 mul), dichloromethane (2 ml) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (46 mg) were added to the compound obtained as a synthetic intermediate in Process 4 of Example 1, that is, a crude material of methyl (2S)-2-amino-3-[4-(1-methyl-2-oxo-1,2-dihydro-3-quinolinyl) phenyl] propionate hydrochloride (30 mg). After stirring the mixture at 30C for 24 hours, the reaction solution was concentrated. After adding ethyl acetate, the mixture was washed with 1N hydrochloric acid, saturated sodium bicarbonate water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate to remove the solvent. The residue was purified with a silica gel chromatography (hexane - ethyl acetate) to obtain the objective compound (40 mg). MS (ESI MH+) : 493 CHNO : C27H22ClFN204

Reference： [1]Patent: EP1454898,2004,A1 .Location in patent: Page 30

19
[ 1056618-50-8 ]
[ 434-75-3 ]
C₂₇H₃₃ClFN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20℃;	To a solution of 36b (3.5 g, 10.0 mmol) in DMF (100 ml) at RT was added <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (1.75g, 10.0 mmol). To the resulting solution were added sequentially EDCI (2.0 g, 10.0 mmol), HOBt (1.35 g, 10.0 mmol) and NaHC03 (3.4g, 40.0 mmol) and the mixture was stirred overnight at RT. The solvent was evaporated under reduced pressure and the residue was dissolved in DCM (100 ml). The organics were washed with 2% HCI, water, saturated. NaHC03 solution, dried (Na2S04) and concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (3.5% MeOH/DCM) to afford 3.3 g (66%) of37a: MS (ES+) m/z 502 (M + H) +.

Reference： [1]Patent: WO2005/121145,2005,A2 .Location in patent: Page/Page column 130-131

20
(E)-2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [ No CAS ]
[ 434-75-3 ]
(E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 28h;	Example 64 (E)-2-(2-Chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [Show Image] Under an argon atmosphere, EDC hydrochloride (39 mg) and HOBT (3 mg) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (51 mg) and <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> in dichloromethane (1.5 ml), and the resulting mixture was stirred at room temperature for 28 hours. To the reaction solution, 1N hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, developing solvent: hexane/ethyl acetate = 1/2) to obtain (E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (39 mg).
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 28h;	Example 64 (E)-2-(2-Chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [Show Image] Under an argon atmosphere, EDC hydrochloride (39 mg) and HOBT (3 mg) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (51 mg) and <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> in dichloromethane (1.5 ml), and the resulting mixture was stirred at room temperature for 28 hours. To the reaction solution, 1N hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, mobile phase: hexane/ethyl acetate = 1/2) to obtain (E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (39 mg).

Reference： [1]Patent: WO2006/68213,2006,A1 .Location in patent: Page/Page column 101-102; 127
[2]Patent: EP2033637,2009,A1 .Location in patent: Page/Page column 70; 71
[3]Patent: EP2042171,2009,A1 .Location in patent: Page/Page column 70

21
[ 902152-86-7 ]
[ 434-75-3 ]
4-(2-chloro-6-fluoro-benzoylamino)-1H-pyrazole-3-carboxylic acid (1-methanesulphonyl-piperidin-4-yl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 3h;	4B. 4-(2-Chloro-6-fluoro-benzoylamino)-1H-pyrazole-3-carboxyric acid (1- niethanesulphonyl-piperidin-4-yl)-amideA solution of 4-amino-1H-pyrazole-3-carboxylic acid (1-methanesulphonyl- piperidin-4-yl) amide (150 mg, 5.23 mmoles), <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (91 mg, 0.523 mmoles), HOBt (85 mg, 0.627 mmoles) and EDC (120 mg, 0.627 mmoles) in DMF (10 ml) was stirred at ambient temperature for 3 hours. The reaction mixture was partitioned between EtOAc and a saturated solution of sodium hydrogen carbonate. The organic portion was washed with water (x2), brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by flash chromatography (Biotage SP4, 25S, flow rate 25ml/min, gradient EtOAc/Petrol (1 :1) to EtOAc) to give 4-(2-chloro-6-fluoro-benzoylamino)-1H-pyrazole-3- carboxylic acid (l-methanesulphonyl-piperidin-4-yl)-amide as a white solid (25 mg, 11%). (LC/MS: Rt 2.57, [M+H]+ 444.22)

Reference： [1]Patent: WO2006/77414,2006,A1 .Location in patent: Page/Page column 165

22
[ 60-29-7 ]
[ 434-75-3 ]
methyl 2-chloro-6-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In methanol;	a Esterification of 2-Chloro-6-fluorobenzoic Acid A 50-mL round-bottom flask was equipped with a magnetic stir bar, reflux condenser, thermometer, nitrogen inlet, and a heating mantle attached to a temperature controller. The flask was charged with <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (8.30 g, 47.55 mmol), methanol (15 g), and concentrated sulfuric acid (1 g). The reaction mixture was heated to 60 C. for seven days, then cooled to room temperature. Ethyl ether (50 mL) was added; the reaction mixture was transferred to a separatory funnel and washed with 1M sodium hydroxide solution (3*40 mL), then with water (40 mL). The organic layer was dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was dried under vacuum to give 5.34 g of methyl 2-chloro-6-fluorobenzoate as a yellow oil.
	With sulfuric acid; In methanol;	a) Preparation of Methyl 2-Chloro-6-fluorobenzoate from 2-Chloro-6-fluorobenzoic Acid Esterification of 2-Chloro-6-fluorobenzoic Acid A 50-mL round-bottom flask was equipped with a magnetic stir bar, reflux condenser, thermometer, nitrogen inlet, and a heating mantle attached to a temperature controller. The flask was charged with <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (8.30 g, 47.55 mmol), methanol (15 g), and concentrated sulfuric acid (1 g). The reaction mixture was heated to 60 C for seven days, then cooled to room temperature. Ethyl ether (50 mL) was added; the reaction mixture was transferred to a separatory funnel and washed with 1 M sodium hydroxide solution (3 x 40 mL), then with water (40 mL). The organic layer was dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure and the residue was dried under vacuum to give 5.34 g of methyl 2-chloro-6-fluorobenzoate as a yellow oil.

Reference： [1]Patent: US5886210,1999,A
[2]Patent: EP825173,1998,A1

23
[ 50541-93-0 ]
copper(II) oxide [ No CAS ]
[ 434-75-3 ]
2-(1-benzyl-4-piperidinylamino)-6-fluorobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide;	Reference Example 34 Potassium carbonate (8.9 g), 4-amino-1-benzylpiperidine (18.5 g), cupric oxide (0.6 g) and dimethylformamide (25 ml) are added to <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (11.3 g) and the mixture is reacted with heating at 140 C. for 6 hours. After the reaction, the solvent is concentrated and to the resulting residue are added water (200 ml) and active carbon (1 g). The mixture is refluxed for 30 minutes. After filtration, the filtrate is cooled and then adjusted to pH 8.0 with diluted hydrochloric acid. The precipitated crystal is collected by filtration and washed successively with water and methanol to give 2-(1-benzyl-4-piperidinylamino)-6-fluorobenzoic acid (7.6 g) as white powders, m.p.: 233-236 C.

Reference： [1]Patent: US5356904,1994,A

24
[ 108-98-5 ]
[ 434-75-3 ]
6-fluoro-2-phenylthiobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) iodide; potassium carbonate; In ethanol; water; nitrobenzene;	The following thiaxanthydrol starting materials were prepared by reduction of the corresponding thiaxanthones in an analogous manner to that described above. 2-methylthiaxanthydrol, m.p. 93C. (from ethanol) 2-hydroxythiaxanthydrol, m.p. 124-126C. 2-chlorothiaxanthydrol, m.p. 126.5C. (from ethanol) 2-methoxythiaxanthydrol, m.p. 103-104C. (from ethanol). The starting material 1-fluorothiaxanthydrol was prepared in the following way. To a stirred mixture of <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (52.4 g.) and nitrobenzene (225 ml.) at 80C. were added anhydrous potassium carbonate (45.6 g.), cuprous iodide (1.5 g.), copper bronze (1.5 g.) and thiophenol (34 ml.). The mixture was stirred at 160-166C. for 6 hours, cooled to room temperature, and shaken with a mixture of ether (1200 ml.) and water (2100 ml.). The aqueous phase was separated, washed with ether, filtered with charcoal and acidified with 5N sulphuric acid to give 6-fluoro-2-phenylthiobenzoic acid, m.p. 152-156C.

Reference： [1]Patent: US3948947,1976,A

25
ethylene dichloride hydrochloride [ No CAS ]
(E)-2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [ No CAS ]
[ 434-75-3 ]
(E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; benzotriazol-1-ol; In dichloromethane;	Example 64 (E)-2-(2-Chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester Under an argon atmosphere, EDC hydrochloride (39 mg) and HOBT (3 mg) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (51 mg) and <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> in dichloromethane (1.5 ml), and the resulting mixture was stirred at room temperature for 28 hours. To the reaction solution, 1N hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, mobile phase: hexane/ethyl acetate = 1/2) to obtain (E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (39 mg).

Reference： [1]Patent: EP1840121,2007,A1

26
[ 54-96-6 ]
[ 434-75-3 ]
[ 1467869-46-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5111 - 5114

27
[ 1600-27-7 ]
[ 434-75-3 ]
mercury(II) 2-chloro-6-fluorobenzoate [ No CAS ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,
Zeitschrift fuer Anorganische und Allgemeine Chemie,1994,vol. 620,p. 993 - 998

28
[ 894401-36-6 ]
[ 434-75-3 ]
(E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 28h;	Under an argon atmosphere, EDC hydrochloride (39 mg) and HOBT (3 mg) were added to a solution of 2-amino-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (51 mg) and <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> in dichloromethane (1.5 ml), and the resulting mixture was stirred at room temperature for 28 hours. To the reaction solution, 1N hydrochloric acid was added, and the resulting mixture was extracted with ethyl acetate. Organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by thin layer chromatography (silica gel, developing solvent: hexane/ethyl acetate = 1/2) to obtain (E)-2-(2-chloro-6-fluorobenzamido)-5-[4-(methyl-pyrimidin-2-ylamino)phenyl]pent-4-enoic acid methyl ester (39 mg).

Reference： [1]Patent: EP2039687,2009,A1 .Location in patent: Page/Page column 69-70

29
[ 844443-81-8 ]
[ 434-75-3 ]
[ 1048675-61-1 ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 4986 - 4999

30
copper(II) chloride monohydrate [ No CAS ]
[ 434-75-3 ]
tetrakis(μ-2-chloro-6-fluorobenzoato-k(2)O,O')bis[aquacopper(II)] [ No CAS ]

Reference： [1]Polyhedron,2009,vol. 28,p. 1320 - 1330

31
[ 434-75-3 ]
[ 206884-30-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; nitric acid; at 0 - 20℃; for 1h;	[00185] Step A: 2-Chloro-6-fluorobenzoic acid (2.00 g, 11.5 mmol) was dissolved in sulfuric acid (20 mL) and cooled to 0C. Nitric acid (0.529 mL, 12.6 mmol) was added, and the reaction mixture was warmed to room temperature for one hour. The reaction mixture was diluted with water, and the aqueous portion was extracted with DCM (3 X), dried over Na2SO4, concentrated to a solid, 2-chloro-6-fluoro-3-nitrobenzoic acid (97%), which was used directly in the next step without further purification.
97%	With sulfuric acid; nitric acid; at 0 - 20℃; for 1h;	2-Chloro-6-fluorobenzoic acid (2.00 g, 11.5 mmol) was dissolved in sulfuric acid (20 mL) and cooled to 0C. Nitric acid (0.529 mL, 12.6 mmol) was added, and the reaction mixture was warmed to room temperature for one hour. The reaction mixture was diluted with water, and the aqueous portion was extracted with DCM (3 X), dried over Na2SO4, concentrated to a solid, 2-chloro-6-fluoro-3-nitrobenzoic acid (97%), which was used directly in the next step without further purification.
97%	With sulfuric acid; nitric acid; at 0 - 20℃; for 1h;	Step A: 2-Chloro-6-fluorobenzoic acid (2.00 g, 11.5 mmol) was dissolved in sulfuric acid (20 mL) and cooled to 0C. Nitric acid (0.529 mL, 12.6 mmol) was added, and the reaction mixture was warmed to room temperature for one hour. The reaction mixture was diluted with water, and the aqueous portion was extracted with DCM (3 X), dried over Na2SO4, concentrated to a solid, 2-chloro-6-fluoro-3-nitrobenzoic acid (97%), which was used directly in the next step without further purification.

97%	With sulfuric acid; nitric acid; at 0 - 20℃; for 1h;	2-Chloro-6-fluorobenzoic acid (2.00 g, 11.5 mmol) was dissolved in sulfuric acid (20 mL) and cooled to 0C. Nitric acid (0.529 mL, 12.6 mmol) was added, and the reaction mixture was warmed to room temperature for one hour. The reaction mixture was diluted with water, and the aqueous portion was extracted with DCM (3 X), dried over Na2SO4, concentrated to a solid, 2-chloro-6-fluoro-3-nitrobenzoic acid (97%), which was used directly in the next step without further purification.
90%	With sulfuric acid; nitric acid; at 20℃; for 30h;	The 2-chloro-6-fluoro benzoic acid (5.0g, 28 . 6mmol) dissolved in concentrated sulfuric acid (15.0 ml) in, under the condition in the ice water bath is added dropwise fuming nitric acid (1.3 ml, 35 . 3mmol), under conditions such that the stirring 10 minutes, removed ice-water bath, stirring at room temperature for 30 minutes. To the reaction liquid is poured into ice water, stirring 10 minutes, ethyl acetate (50 ml * 3) extraction, liquid, organic phase with saturated salt water, dried with anhydrous sodium sulfate and concentrated in vacuo to obtain the target product (5.7g, 90%).
82.2%		Stepl. 2-Chloro-6-fluoro-3-nitrobenzoic acid. To a 50 mL single-neck round- bottom flask <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong>(3.0 g, 17.1 mmol, l.Oeq) was added to H2SO4 (30 g) at 0 C under an atmosphere of nitrogen and stirred for 1 hour. Then HNO3 (1.90 g, 20.6 mmol, 1.2 eq) was added dropwise to the reaction mixture. The resulting mixture was stirred for 1 hour. The reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (50 mL x 3). The organic layers were combined, dried over anhydrous sodium sulfate, filtrated and concentrated to give 2-chloro-6-fluoro-3-nitrobenzoic acid (3.1 g) as a solid. Yield: 82.2%.

Reference： [1]Patent: WO2011/25951,2011,A1 .Location in patent: Page/Page column 34
[2]Patent: WO2009/111277,2009,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2009/111280,2009,A1 .Location in patent: Page/Page column 41
[4]Patent: WO2009/111279,2009,A1 .Location in patent: Page/Page column 69
[5]Patent: CN103102349,2017,B .Location in patent: Paragraph 0297-0299
[6]Patent: WO2012/138809,2012,A1 .Location in patent: Page/Page column 15

32
C₆₄H₆₉F₂N₈O₁₅P [ No CAS ]
[ 434-75-3 ]
C₇₁H₇₁ClF₃N₈O₁₆P [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 13072 - 13079

33
[ 136-95-8 ]
[ 434-75-3 ]
[ 1120366-09-7 ]

Reference： [1]Magnetic Resonance in Chemistry,2009,vol. 47,p. 174 - 178

34
[ 434-75-3 ]
[ 1206164-19-3 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 9350 - 9354
[2]Organic Letters,2010,vol. 12,p. 1000 - 1003

35
[ 3581-91-7 ]
[ 434-75-3 ]
[ 1218780-38-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1564 - 1567

36
[ 95-16-9 ]
[ 434-75-3 ]
2-(2-chloro-6-fluorophenyl)benzo[d]thiazole [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5589 - 5592
[2]Organic Letters,2010,vol. 12,p. 1564 - 1567

37
[ 5404-86-4 ]
[ 434-75-3 ]
[ 1233081-06-5 ]

Yield	Reaction Conditions	Operation in experiment
12%		-chloro-6-fluoro-LambdaT-(9H-purin-6-yl)benzohydrazideTo a solution of <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (0.52 g, 3.0 mmol) in anhydrous Lambda/,Lambda/-dimethyl-formamide (20 ml_) was added O-benzotriazole- Lambda/,Lambda/,Lambda/',Lambda/'-tetramethyl uronium hexafluoro-phosphate (HBTU, 1.14 g, 3.0 mmol). The solution was stirred at room temperature for 10 minutes then diisopropylethylamine (0.77 g, 6.0 mmol) and 6-hydrazinyl-9H-purine (0.45 g, 3.0 mmol) were added to the reaction mixture. The reaction was flushed with argon and stirred at 75C for 18 hours overnight. The reaction was transferred to a separatory funnel containing water (100 ml_) and diluted with ethyl acetate (75 ml_). The layers were shaken and separated, and the aqueous layer was concentrated in vacuo to give a dark brown solid. The crude solid was recrystallized in hot ethanol to give a beige powder (110 mg, 12%). 1H- NMR (400 MHz, d6-DMSO) delta 13.11 (s, 1 H), 10.69 (s, 1H), 9.87 (s, 1 H), 8.30- 8.20 (m, 2H), 7.58-7.49 (m, 1H), 7.44-7.38 (m, 1 H), 7.34 (t, J = 8.40 Hz, 1 H); Mass spectrum (ESI +ve) m/z 307.0 (MH+, 35CI), 309.0 (MH+, 37CI).

Reference： [1]Patent: WO2010/74746,2010,A1 .Location in patent: Page/Page column 89-90

38
[ 913570-34-0 ]
[ 434-75-3 ]
[ 1253188-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 16.1667h;	Example 180: 2-Chloro-Lambda/-H -(( 5-chloro-2-r(phenylmethyl)oxy1phenyl)methyl)- 1H-pyrazol-3-yll-6-fluorobenzamide; To a solution of <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (18 mg, 0.1 mmol, Aldrich) in DMF (0.1 ml) was added a solution of HATU (38 mg, 0.1 mmol) in DMF (0.2 ml). After 5 min, DIPEA (0.050 ml, 0.27 mmol) was added to the mixture. To the mixture was added a solution of 1-({5-chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1 H-pyrazol-3-amine (for a preparation see Intermediate 55)(0.1 mmol) in DMF (0.1 ml). After shaking for 10 min, the resulting solution was allowed to stand for 16 h at ambient temperature. The solvent was removed using a genevac. The sample was dissolved in 1 :1 MeOH:DMSO (0.6 ml) and purified by MDAP on a C18 column using Acetonitrile- Water with a TFA modifier (Method D). The solvent was evaporated in vacuo using the Genevac to give the title compound; LCMS (System 3) MH+ = 470/472, tRET = 1.32 min.

Reference： [1]Patent: WO2010/122089,2010,A1 .Location in patent: Page/Page column 143

39
[ 925252-73-9 ]
[ 434-75-3 ]
3-butyl-8-chloro-1-{4-[5-(2-chloro-6-fluorophenyl)-1,2,4-oxadiazol-3-yl]-butyl}-3,7-dihydro-1H-purine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%		Example 140: 3-Butyl-8<:hloro-144-r5-(2-chloro-6-fluorophenyl)-1.2.4-oxadiazol-3- v?butyl>-3.7-dihvdro-1H-purine-2.6-dione2-Chloro-6-fluorobenzoic acid (44mg, 0.25mmol) and CDI (45mg, 0.28mmol) were stirred in anhydrous DMSO (0.9ml) at rt for 1 h. (1Z)-5-(3-Butyl-8-chloro-2,6-dioxo- 2,3,6,7-tetrahydro-1/-/-purin-1-yl)-Lambda/-hydroxypentanimidamide (100mg, 0.28mmol) was added and the mixture was stirred at 9O0C for 16h. The mixture was purified by MDAP.The product fraction was combined and concentrated to give the title compound as a white solid (6.4mg, 5%).LC/MS: m/z 495 [MH]+, RT 3.58min.

Reference： [1]Patent: WO2007/17261,2007,A1 .Location in patent: Page/Page column 101

40
[ 434-75-3 ]
[ 1186194-01-3 ]

Reference： [1]Patent: WO2011/25951,2011,A1
[2]Patent: CN103102349,2017,B
[3]Patent: WO2009/111277,2009,A1
[4]Patent: WO2009/111280,2009,A1

41
[ 434-75-3 ]
[ 1294494-80-6 ]

Reference： [1]Patent: WO2011/48004,2011,A1
[2]Patent: US2011/263556,2011,A1

42
[ 434-75-3 ]
[ 1294552-10-5 ]

Reference： [1]Patent: WO2011/48004,2011,A1
[2]Patent: US2011/263556,2011,A1

43
[ 50667-69-1 ]
[ 434-75-3 ]
[ 1294496-80-2 ]

Yield	Reaction Conditions	Operation in experiment
23%	With sulfuric acid; at 20℃;Cooling with ice;	(a) 2-Chlor-6-flour-3-(trifluormethylcarbonylamino)methyl-benzoic acidN-(Hydroxymethyl)trifluoracetamide (0,82 g; 5,73 mmol) was added to a mixture of 10 mL cone. H2S04 and 2-chlor-6-fluorbenzoic acid (1 g; 5,73 mmol) under ice bath cooling and stirred at rt overnight. The mixture was poured into ice, DCM was added, the resulting precipitate was filtered, washed with DCM and water and dried. The residue was purified by HPLC.Yield: 400 mg (23%; Purity: 95%) MS: [M-H]" = 298
23%	With sulfuric acid; at 20℃;	N-(Hydroxymethyl)trifluoracetamide (0.82 g; 5.73 mmol) was added to a mixture of 10 mL conc. H2SO4 and <strong>[434-75-3]2-chlor-6-fluorobenzoic acid</strong> (1 g; 5.73 mmol) under ice bath cooling and stirred at rt overnight. The mixture was poured into ice, DCM was added, the resulting precipitate was filtered, washed with DCM and water and dried. The residue was purified by HPLC.Yield: 400 mg (23%; Purity: 95%) MS: [M-H]-=298

Reference： [1]Patent: WO2011/48004,2011,A1 .Location in patent: Page/Page column 92
[2]Patent: US2011/263556,2011,A1 .Location in patent: Page/Page column 44

44
[ 434-75-3 ]
[ 1094457-24-5 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2594 - 2596

45
[ 434-75-3 ]
(2-chloro-6-fluorophenyl)(phenyl)methanone [ No CAS ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2594 - 2596
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 5085 - 5089
Angew. Chem.,2019,vol. 131,p. 5139 - 5143,5

46
[ 552-16-9 ]
[ 434-75-3 ]
[ 2436-96-6 ]
[ 1352638-60-8 ]
[ 1352638-63-1 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 5787 - 5790

47
[ 3113-72-2 ]
[ 434-75-3 ]
[ 1352638-63-1 ]
[ 1352638-62-0 ]
[ 114324-70-8 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 5787 - 5790

48
[ 2516-95-2 ]
[ 434-75-3 ]
[ 1352638-63-1 ]
[ 1352638-61-9 ]
[ 19036-42-1 ]

Reference： [1]European Journal of Organic Chemistry,2011,p. 5787 - 5790

49
[ 494769-44-7 ]
[ 434-75-3 ]
[ 1363397-35-6 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 8h;	General procedure: The intermediate (3) (0.5 g, 0.00217 mol), EDCl (0.622 g, 0.00325 mol), DMAP (0.345 g, 0.0028 mol) were stirred in dichloromethane (6 mL) at 0 C, and the substituted acid (0.00217 mol) were dissolved in (4 mL) of dichloromethane and charged to the reaction mixture and stirred at room temperature for 8 h. The reaction completion was monitored by TLC. Reaction was completed. The reaction mixture was diluted with (10 mL) of dichloromethane, and was washed with 10% NaHCO3 (10 mL). Separated the organic layer and was washed with saturated brine solution (10 mL). The organic layer was dried over sodium sulfate and concentrated the organic layer under reduced pressure to afford compounds 4a-t. The spectral data of compounds 4(a-t) are given below.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 49,p. 172 - 182

50
[ 434-75-3 ]
[ 935984-69-3 ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 240 - 245

51
[ 434-75-3 ]
[ 1363189-03-0 ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 240 - 245

52
[ 434-75-3 ]
[ 1363189-44-9 ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 240 - 245

53
[ 434-75-3 ]
[ 1363189-63-2 ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 240 - 245

54
[ 434-75-3 ]
[ 1363189-23-4 ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 240 - 245

55
[ 1374298-77-7 ]
[ 434-75-3 ]
[ 1374298-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; for 18h;	Step 2 -Preparation of methyl 2-(2-chloro-6-fluorobenzamido)-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate To a solution of methyl 2-amino-7,7-dimethyl-7,8-dihydro-1H-benzofuro[4,5-d]imidazole-5-carboxylate (1.00 g, 3.81 mmol) in THF (25 mL) was added EDCI.HCl (1.4 g, 7.62 mmol), HOBT (1.00 g, 7.62 mmol), <strong>[434-75-3]2-chloro-6-fluorobenzoic acid</strong> (1.32 g 7.62 mmol) and TEA (3 mL). The reaction mass was stirred for 18 h. The reaction mass was quenched in water extracted with 10% DCM: methanol. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on basic alumina eluting with 0.7% DCM: MeOH to afford 0.700 g of the desired product. 1HNMR (DMSO-d6): delta 1.43 (s, 6H), 3.02 (s, 2H), 3.58 (s, 3H), 6.08 (bs, 1H), 7.59-7.69 (m, 2H), 7.83 (q, J=6.6 Hz, 1H), 8.14 (bs, 2H); MS [M+H]+: 418.05.

Reference： [1]Patent: US2012/108583,2012,A1 .Location in patent: Page/Page column 39

56
[ 434-75-3 ]
[ 1254566-97-6 ]