[ CAS No. 455-67-4 ] {[proInfo.proName]}

Name: 455-67-4|1-(3-Fluorophenyl)propan-1-one|97%
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SKU: A160974
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Quality Control of [ 455-67-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 455-67-4 ]

Product Details of [ 455-67-4 ]

CAS No. :	455-67-4	MDL No. :	MFCD00061245
Formula :	C₉H₉FO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RPMOHVRRKYJFSB-UHFFFAOYSA-N
M.W :	152.17	Pubchem ID :	521183
Synonyms :

Calculated chemistry of [ 455-67-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.4
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	2.84
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	2.91
Consensus Log Po/w :	2.51

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.47
Solubility :	0.52 mg/ml ; 0.00342 mol/l
Class :	Soluble
Log S (Ali) :	-2.23
Solubility :	0.888 mg/ml ; 0.00583 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.4
Solubility :	0.0606 mg/ml ; 0.000398 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 455-67-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 455-67-4 ]

* 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 [ 455-67-4 ]
Downstream synthetic route of [ 455-67-4 ]

[ 455-67-4 ] Synthesis Path-Upstream 1~14

1
[ 701-38-2 ]
[ 455-67-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 1995, vol. 30, # 1, p. 85 - 94
[2] Patent: US2008/221358, 2008, A1, . Location in patent: Page/Page column 4
[3] Patent: WO2007/15259, 2007, A2, . Location in patent: Page/Page column 10

2
[ 701-38-2 ]
[ 455-67-4 ]

Reference： [1] Organic Letters, 2007, vol. 9, # 5, p. 865 - 868

3
[ 30984-53-3 ]
[ 455-67-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5613 - 5616

4
[ 403-54-3 ]
[ 925-90-6 ]
[ 455-67-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 3, p. 761 - 765[2] Angew. Chem., 2014, vol. 126, # 3, p. 908

5
[ 74-96-4 ]
[ 403-54-3 ]
[ 455-67-4 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1661 - 1667

6
[ 462-06-6 ]
[ 79-03-8 ]
[ 455-67-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 48, p. 11651 - 11656

7
[ 462-06-6 ]
[ 123-62-6 ]
[ 455-67-4 ]

Reference： [1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 123 - 136

8
[ 701-38-2 ]
[ 455-67-4 ]

Reference： [1] Chemical Science, 2017, vol. 8, # 11, p. 7476 - 7482

9
[ 1073-06-9 ]
[ 455-67-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 20, p. 5613 - 5616

10
[ 456-48-4 ]
[ 455-67-4 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1661 - 1667

11
[ 458-02-6 ]
[ 455-67-4 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1661 - 1667

12
[ 455-67-4 ]
[ 100286-90-6 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1661 - 1667

13
[ 455-67-4 ]
[ 97682-44-5 ]

Reference： [1] Synthetic Communications, 2013, vol. 43, # 12, p. 1661 - 1667

14
[ 455-67-4 ]
[ 1168139-41-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 18, p. 5907 - 5922

[ 455-67-4 ] Synthesis Path-Downstream 1~88

1
[ 455-67-4 ]
[ 4301-14-8 ]
[ 159028-55-4 ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1111 - 1118

2
[ 50-00-0 ]
[ 455-67-4 ]
[ 25150-61-2 ]
1-(3-Fluoro-phenyl)-2-methyl-3-pyrrolidin-1-yl-propan-1-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1995,vol. 30,p. 85 - 94

3
[ 701-38-2 ]
[ 455-67-4 ]

Yield	Reaction Conditions	Operation in experiment
	With Jones reagent; In acetone; at 0 - 10℃; for 3h;	Example 2Preparation of 3-fluoropropiophenone350 ml of Jones reagent was added dropwise to 100 g of 1-(3-fluorophenyl)propan-1-ol in 1 L of acetone at 0 to 10 C., over a period of two hours. The reaction solution was stirred at 0 to 10 C. for additional 1 hour. The solvent was removed in vacuo. The reaction solution was extracted with 400 ml of DCM and organic layer was dried over sodium sulfate. The solvent was removed in vacuo. After drying, 120 g of 3-fluoropropiophenone were obtained as a yellow oil and taken as such to the next step 1H NMR (CDCl3): delta=1.3 (t, 3H, -CH2-CH3, 2.95 (q, 2H, CO-CH2-CH3), 7.25 (m, 1H, Ar 5-H), 7.43 (m, 1H, Ar-4H), 7.63 (q, 1H, Ar-6H), 7.75 (bd, 1H, Ar-4H)
	With Jones reagent; In acetone; at 0 - 10℃; for 3h;	Example 2:Preparation of 3-fluoropropiophenone350 ml of Jones reagent was added dropwise to 100 g of l-(3-fluorophenyl)propan-l- ol in 1 L of acetone at 0 to 10 C, over a period of two hours. The reaction solution was stirred at 0 to 10 C for additional 1 hour. The solvent was removed in vacuo. The reaction solution was extracted with 400 ml of DCM and organic layer was dried over sodium sulfate. The solvent was removed in vacuo. After drying, 120 g of 3- fluoropropiophenone were obtained as a yellow oil and taken as such to the next step1HNMR (CDCl3): delta= 1.3(t, 3H, -CH2- CH2), 2.95 (q, 2H, CO-CjJb-CH3), 7.25 (m,IH, Ar_5-H), 7.43 (m, IH, Ar-4H), 7.63 (q, 1 H, Ar-6H), 7.75 (bd, IH, Ar-4H)

Reference： [1]European Journal of Medicinal Chemistry,1995,vol. 30,p. 85 - 94
[2]Patent: US2008/221358,2008,A1 .Location in patent: Page/Page column 4
[3]Patent: WO2007/15259,2007,A2 .Location in patent: Page/Page column 10

4
[ 701-38-2 ]
[ 455-67-4 ]
(R)-1-(3-fluoro-phenyl)-propan-1-ol [ No CAS ]
(S)-1-(3'-fluorophenyl)propan-1-ol [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 865 - 868

5
[ 455-67-4 ]
3-acetoxy-3-(3-fluorophenyl)pent-1-yne [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1111 - 1118

6
[ 455-67-4 ]
(R)-3-(3-Fluoro-phenyl)-pent-1-yn-3-ol [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1111 - 1118

7
[ 455-67-4 ]
3-(3-fluorophenyl)pent-1-yne-3-ol [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1994,vol. 5,p. 1111 - 1118

8
[ 455-67-4 ]
[ 91-56-5 ]
[ 844470-95-7 ]

Yield	Reaction Conditions	Operation in experiment
56%	With hydrogenchloride; acetic acid; In water; for 20h;Heating / reflux;	Intermediate 1 : 3-Methyl-2-(3-fluorophenyl)-4-quinolinecarboxylic acid A stirred mixture of isatin (9.7g, 66mmole) and <strong>[455-67-4]3-fluoropropiophenone</strong> (1Og, 66mmole) in acetic acid (50ml) at 750C was treated with cone. HCI acid (120ml) and then heated at reflux temperature for 2Oh. The reaction mixture was allowed to cool, then poured into water (500ml) with good stirring. After a few minutes, the precipitate was filtered off, washed with water, then Et2O, and dried. The solid was washed further by stirring in 2:1 Et2O/EtOAc (150ml) for 0.25h, then filtered and dried to afford the title compound as a pale brown solid (10.3g, 56%); 1 HNMR (400MHz, d6DMSO): delta 2.39 (3H, s), 7.32 - 7.40 (1H, m), 7.42 - 7.52 (2H, m), 7.53 - 7.61 (1H, m), 6.67-7.73 (1H, m), 7.76 - 7.85 (2H, m), 8.06 (1 H, d).
56%	With hydrogenchloride; acetic acid; at 75℃; for 20h;Heating / reflux;	Intermediate 1 : 3-Methyl-2-(3-fluorophenyl)-4-quinolinecarboxylic acid A stirred mixture of isatin (9.7g, 66mmole) and <strong>[455-67-4]3-fluoropropiophenone</strong> (10g, 66mmole) in acetic acid (50ml) at 750C was treated with cone. HCI acid (120ml) and then heated at reflux temperature for 2Oh. The reaction mixture was allowed to cool, then poured into water (500ml) with good stirring. After a few minutes, the precipitate was filtered off, washed with water, then Et2O, and dried. The solid was washed further by stirring in 2:1 Et2O/EtOAc (150ml) for 0.25h, then filtered and dried to afford the title compound as a pale brown solid (10.3g, 56%); 1 HNMR (400MHz, d6DMSO): delta 2.39 (3H, s), 7.32 - 7.40 (1 H, m), 7.42 - 7.52 (2H, m), 7.53 - 7.61 (1 H, m), 6.67-7.73 (1 H, m), 7.76 - 7.85 (2H, m), 8.06 (1 H, d).
56%	With hydrogenchloride; acetic acid; In water; at 75℃; for 20h;Heating / reflux;	Intermediate 1 : 3-Methyl-2-(3-fluorophenyl)-4-quinolinecarboxylic acid; A stirred mixture of isatin (9.7g, 66mmole) and <strong>[455-67-4]3-fluoropropiophenone</strong> (1Og, 66mmole) in acetic acid (50ml) at 750C was treated with cone. HCI acid (120ml) and then heated at reflux temperature for 2Oh. The reaction mixture was allowed to cool, then poured into water (500ml) with good stirring. After a few mins., the precipitate was filtered off, washed with water, then Et2O, and dried. The solid was washed further by stirring in 2:1 Et2O/EtOAc (150ml) for 0.25h, then filtered and dried to afford the title compound as a pale brown solid (10.3g, 56%); 1 HNMR (400MHz, d6DMSO) delta 2.39 (3H, s), 7.32 - 7.40 (1 H, m), 7.42 - 7.52 (2H, m), 7.53 - 7.61 (1 H, m), 6.67-7.73 (1 H, m), 7.76 - 7.85 (2H, m), 8.06 (1 H, d).

26%

. SATIN (9.7 g, 66 mmol, 1EQ) was stirred in glacial acetic acid (180 mL) at room temperature and <strong>[455-67-4]3-fluoropropiophenone</strong> (10 g, 66 mmol, 1EQ) added. The reaction was then heated to 75 DEGC. After 10 minutes, conc HCI (66 mL) was added (to give a dark red solution) and the reaction subsequently heated at 105 deg C for 15 hrs. After cooling to room temperature, water (330 mL) was added to afford a beige solid which was collected by filtration and washed with water. Further solid precipitated from the mother liquors on standing. After 2 hrs a second batch of material was collected and washed with water and ether. Combining both batches afforded 4.87g (26%) of the title compound; m/z (APCI) : 282 [M+H] +

Reference： [1]Patent: WO2006/50989,2006,A1 .Location in patent: Page/Page column 16
[2]Patent: WO2006/50991,2006,A1 .Location in patent: Page/Page column 21
[3]Patent: WO2006/50992,2006,A1 .Location in patent: Page/Page column 21
[4]Patent: WO2005/14575,2005,A1 .Location in patent: Page/Page column 27

9
[ 455-67-4 ]
[ 100-97-0 ]
[ 860456-47-9 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; at 80℃; for 4h;	Example 1; Preparation of 6-fluoro-2-methyl-1-indanone; 10 g of 3-fluoropropriophenone, 12.8 g of HMTA (hexamethylentetramine) and 14 g of acetic anhydride were charged into a 50-ml reactor pretreated with two cycles of vacuum and nitrogen and heated at 80C for 4 hours. The reaction mixture was cooled at 30C and a mixture of 76.8 g of dichlorometane and 68.6 ml of NaOH 2N was added thereto. The obtained mixture was stirred for 1 hour at 35C. The phases were separated and 29.4 ml of HC1 IN were added to the organic phase, by keeping the so-obtained mixture under stirring for 3 hours at 30C. The phases were separated again and 57.6 g of dichlorometane were added to the aqueous phase. The obtained mixture was left under stirring for 1 hour at 30C, the phases were separated once more, and the obtained organic phase was added to the preceding one and concentrated by vacuum-distillation to 14 ml volume. The concentrated organic phase containing (3-fluorophenyl)-isopropenyl-ketone (VIII) was slowly added in 30 minutes to a solution of 70.4 g of 96% HIS04 preheated at 60C. The temperature was maintained constant and dichlorometane was removed by distillation. The reaction mixture was then cooled to 25C and added into a mixture of 58 g of H2O and 77.8 g of dichlorometane kept at 15C. The temperature was maintained below 30C. The solution was stirred for 3 hours at 30C and the phases were separated. The aqueous phase was extracted with 38.4 g of dichlorometane, for 2 hours at 30C. The organic phase was separated, added to the previously obtained one, and the solvent removed under reduced pressure. The so-obtained dry residue was a mixture of 6.2 g of 6-fluorine-2-methyl-1-indanone (I) and 4-fluorine-2- methyl-1-indanone (IX), wherein the ratio between the two regioisomers was 10: 1. In order to determine the regioisomeric ratio, the gas-chromatography was used. The 4- fluoro-2-methyl-1-indanone (IX) regioisomer showed a peak at the retention time (Rt) of 13.1 whereas the desired 6-fluoro-2-methyl-1-indanone (1) regioisomer showed a peak at Rt =13.5 (DB-1701 column, 30-m length and inner diameter equal to 0.32 mm, 80C starting temperature, increased by 10C/min until 200C, then after 6 minutes increased by 10C/min until 240C, temperature kept for 17 minutes).

Reference： [1]Patent: WO2005/68411,2005,A1 .Location in patent: Page/Page column 5-6

10
[ 455-67-4 ]
[ 924648-17-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With nitric acid; at -5 - 5℃; for 10h;	Example 3Preparation of 5-fluoro-2-nitropropiophenone3 L of fuming nitric acid was added dropwise to 1 kg of <strong>[455-67-4]3-fluoropropiophenone</strong> at -5 to 5 C., over a period of eight hours. The reaction solution was stirred at 0 C. for two hours. The reaction solution was carefully poured on crushed ice and stirred for 1 hour. The cold solution was filtered and the solids obtained were extracted with 6 L of DCM. The organic layer was separated and washed twice with 3 L of 5% NaHCO3 solution each time and the combined DCM extracts were dried over sodium sulfate. The solvent was removed in vacuo. After drying, 775 g (98%) of 5-fluoro-2-nitropropiophenone were obtained as a yellow liquid, taken as such to next step.1HNMR (CDCl3): delta=1.25 (t, 3H, -CH2-CH3), 2.75 (q, 2H, CO-CH-CH3), 7.06 (m, 1H, Ar H), 7.28 (m, 1H, Ar H), 8.22 (m, 1H, Ar H).
98%	With nitric acid; at -5 - 5℃; for 10h;	Example 3:Preparation of 5-fluoro-2-nitropropiophenone3 L of fuming nitric acid was added dropwise to 1 kg of <strong>[455-67-4]3-fluoropropiophenone</strong> at -5 to 5 C, over a period of eight hours. The reaction solution was stirred at 0 C for two hours. The reaction solution was carefully poured on crushed ice and stirred for 1 hour. The cold solution was filtered and the solids obtained were extracted with 6 L of DCM. The organic layer was separated and washed twice with 3 L of 5% NaHCO3 solution each time and the combined DCM extracts were dried over sodium sulfate. The solvent was removed in vacuo. After drying, 775 g (98%) of 5-fluoro-2- nitropropiophenone were obtained as a yellow liquid, taken as such to next step. 1HNMR (CDCl3): delta= 1.25(t, 3H, -CH2-CH1), 2.75 (q, 2H, CO-CH5-CH3), 7.06 (m, IH, Ar H), 7.28 (m, IH, Ar H), 8.22 (m, IH, Ar H).

Reference： [1]Patent: US2008/221358,2008,A1 .Location in patent: Page/Page column 4-5
[2]Patent: WO2007/15259,2007,A2 .Location in patent: Page/Page column 9
[3]Synthetic Communications,2013,vol. 43,p. 1661 - 1667

11
[ 455-67-4 ]
(R)-1-(3-fluoro-phenyl)-propan-1-ol [ No CAS ]
(S)-1-(3'-fluorophenyl)propan-1-ol [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2008,vol. 19,p. 1992 - 1997

12
[ 455-67-4 ]
(+)-MTPA chloride [ No CAS ]
C₁₉H₁₈F₄O₃ [ No CAS ]
C₁₉H₁₈F₄O₃ [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2008,vol. 19,p. 1992 - 1997

13
[ 455-67-4 ]
[ 627906-96-1 ]
[ 1188303-86-7 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4410 - 4413

14
[ 455-67-4 ]
[ 92821-83-5 ]

Yield	Reaction Conditions	Operation in experiment
83%		Synthesis of 2-(te^-Butylamino)-<strong>[455-67-4]3'-fluoropropiophenone</strong> (2c)Step 1. 2-Bromo-<strong>[455-67-4]3'-fluoropropiophenone</strong> (10c). To a solution of 2.28 g (0.015 mol) of <strong>[455-67-4]3-fluoropropiophenone</strong>, 9c, in 60 mL of CH2Cl2 was added ten drops of bromine. After stirring at room temperature under nitrogen for several min, the characteristic red color of bromine disappeared, indicating initiation of the reaction. The remainder of the 0.7 mL (15 mmol) of bromine was added drop-wise, and the reaction solution was allowed to stir at room temperature under nitrogen for H h. The reaction solution was quenched and brought to a pH of 9 with a saturated sodium bicarbonate solution. The product was extracted with methylene chloride, dried (Na2SO4), and filtered. The solvent was removed, and the resulting residue was dried briefly under high vacuum to give 3.39 g of a clear oil. Purification by flash chromatography (silica, 5:1 hexane-methylene chloride) gave 2.87 g (83%) of 10c as a clear oil. 1H NMR (CDCl3) delta 7.82-7.73 (dd, IH), 7.69 (d, IH), 7.52-7.43 (m, IH), 7.33-7.29 (m, IH), 5.30-5.18 (q, IH), 1.91 (d, 3H).
76.3%	With copper(ll) bromide; In chloroform; ethyl acetate; for 4h;Reflux;	General procedure: To a stirred solution of benzo[b]thiophene (5.0 g, 37.3 mmol) in CH2Cl2 (60 mL) was added dropwise aluminum chloride (6.5 g, 48.4 mmol) at room temperature. After completion of addition, the mixture was stirred at the same temperature for 10 min. The reaction was cooled to 0, a solution of propionic anhydride (5.8 g, 44.7 mmol) in CH2Cl2 (20 mL) was added dropwise and stirred at the same temperature for 1 h. Quenched the reaction by the addition of water (30 mL). The organic layer were washed with water (50 mL), brine (50 mL) and dried over anhydrous sodium sulfate, and solvent was removed under reduced pressure. The crude residue was purified by silica gel column chromatography using EtOAc/hexane (1/20, v/v) as mobile phase to give 9a (6.2 g, 61.7%) as a white solid. To a stirred solution of 9a (6.2 g, 32.6 mmol) in EtOAc/CHCl3 (40 mL/40 mL) was added CuBr2 (15.1 g, 65.3 mmol). The reaction mixture was slowly heated to reflux, and the refluxing was continued for 4 h. After the mixture was cooled to room temperature, filtered, and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography using EtOAc/hexane (1/20, v/v) as mobile phase to give compound 10a (7.3 g, 83.2%) as a white solid.
	With bromine; In dichloromethane; at 20℃;	Preparation of PAL-587; l -(3-fluorophenyl)propan-l-one (4.53g, leq) and bromine (1.53mL, leq) were combined and stirred in 50mL of methylene chloride overnight at room temperature. The next day the mixture was washed with water (4 x 50mL), brine (2 x 50mL), and dried over anhydrous sodium sulfate. After filtration the volatiles were removed under reduced pressure affording 6.435g (94%) of crude 2- bromo- 1 - 3 -fluoropheny l)propan- 1 -one .

	With bromine; In dichloromethane; acetic acid; at 20℃;	To a stirred solution of <strong>[455-67-4]3'-fluoropropiophenone</strong> (26.287 mmol, 1 eq) in AcOH (35 mL) at RT is slowly added a solution of Br2 (26.287 mL, 1 eq) in DCM (10 mL). The resulting light yellow solution is stirred at RT overnight, concentrated under reduced pressure and the residue diluted with sat. NaHC03. The aq. phase is extracted with EtOAc (3 times). The combined organic layers are washed with with sat. NaHC03 and brine, dried over Na2S04, filtered, and concentrated under reduced pressure to give 2-bromo-1-(3-fluorophenyl)propan- 1-one (5.82 g) as a light yellow oil. The crude is used in the next step without further purification. LC-MS (conditions A): tR = 0.82 min, [M + 1]+ = not detactable. 1H NMR (D6- DMSO): £7.87 (m, 1 H), 7.80 (m, 1 H), 7.61 (m, 1 H), 7.52 (m, 1 H), 5.79 (t, J = 6.0 Hz, 1 H), 1.77 (d, J = 6.0 Hz, 3 H).
	With bromine; acetic acid; In dichloromethane; at 20℃;	To a stirred solution of <strong>[455-67-4]3'-fluoropropiophenone</strong> (26.287 mmol, 1 eq) in AcOH (35 mL) at RT is slowly added a solution of Br2 (26.287 mL, 1 eq) in DCM (10 mL). The resulting light yellow solution is stirred at RT overnight, concentrated under reduced pressure and the residue diluted with sat. NaHC03. The aq. phase is extracted with EtOAc (3 times). The combined organic layers are washed with with sat. NaHC03 and brine, dried over Na2S04, filtered, and concentrated under reduced pressure to give 2-bromo-1-(3-fluorophenyl)propan- 1-one (5.82 g) as a light yellow oil. The crude is used in the next step without further purification. LC-MS (conditions A): tR = 0.82 min, [M + 1]+ = not detactable. 1H NMR (D6- DMSO): £7.87 (m, 1 H), 7.80 (m, 1 H), 7.61 (m, 1 H), 7.52 (m, 1 H), 5.79 (t, J = 6.0 Hz, 1 H), 1.77 (d, J = 6.0 Hz, 3 H).

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6768 - 6781
[2]Patent: WO2010/121022,2010,A1 .Location in patent: Page/Page column 63-64
[3]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136
[4]Journal of Medicinal Chemistry,2010,vol. 53,p. 2204 - 2214
[5]Patent: WO2011/146850,2011,A1 .Location in patent: Page/Page column 52
[6]Patent: WO2012/85857,2012,A1 .Location in patent: Page/Page column 71
[7]Patent: WO2012/85852,2012,A1 .Location in patent: Page/Page column 62

15
[ 455-67-4 ]
[ 69739-34-0 ]
[ 1231952-01-4 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 4731 - 4748

16
[ 110-91-8 ]
[ 455-67-4 ]
C₁₃H₁₆FNO [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2961 - 2970

17
[ 455-67-4 ]
[ 1314018-62-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2961 - 2970

18
[ 455-67-4 ]
C₁₇H₁₁BrClFN₂O [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2961 - 2970

19
[ 455-67-4 ]
[ 1284281-40-8 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2961 - 2970

20
[ 455-67-4 ]
[ 1284281-61-3 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 2961 - 2970

21
[ 455-67-4 ]
[ 1350768-21-6 ]

Reference： [1]Patent: WO2011/146850,2011,A1

22
[ 455-67-4 ]
[ 1384067-11-1 ]

Reference： [1]Patent: WO2012/85852,2012,A1
[2]Patent: WO2012/85857,2012,A1

23
[ 455-67-4 ]
[ 1384067-23-5 ]

Reference： [1]Patent: WO2012/85857,2012,A1
[2]Patent: WO2012/85852,2012,A1

24
[ 455-67-4 ]
[ 1188043-08-4 ]

Reference： [1]Patent: WO2012/85852,2012,A1
[2]Patent: WO2012/85857,2012,A1

25
[ 455-67-4 ]
1-(3-fluorophenyl)-2-hydroxypropan-1-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6749 - 6753
[2]Journal of Organic Chemistry,2017,vol. 82,p. 2219 - 2222
[3]Patent: WO2012/85852,2012,A1
[4]Patent: WO2012/85857,2012,A1

26
[ 455-67-4 ]
[ 1384067-13-3 ]

Reference： [1]Patent: WO2012/85852,2012,A1
[2]Patent: WO2012/85857,2012,A1

27
[ 552-16-9 ]
[ 455-67-4 ]
[ 912654-59-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 8032 - 8036

28
[ 552-16-9 ]
[ 455-67-4 ]
2-(3-fluorophenyl)quinoline [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 8032 - 8036

29
[ 462-06-6 ]
[ 123-62-6 ]
[ 455-67-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136

30
[ 455-67-4 ]
erythro-2-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(3-fluorophenyl)propan-1-ol hydrochloride [ No CAS ]
threo-2-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(3-fluorophenyl)propan-1-ol hydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136

31
[ 455-67-4 ]
2-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)-1-(3-fluorophenyl)propan-1-ol [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136

32
[ 455-67-4 ]
[ 1394148-26-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136

33
[ 455-67-4 ]
[ 1394204-85-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 54,p. 123 - 136

34
[ 110-91-8 ]
[ 455-67-4 ]
[ 1432906-14-3 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 14638 - 14642

35
[ 554-14-3 ]
[ 455-67-4 ]
[ 1440663-23-9 ]

Yield	Reaction Conditions	Operation in experiment
80%	With silver (II) carbonate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; lithium acetate; palladium diacetate; tricyclohexylphosphine; In 1,2-dimethoxyethane; at 100℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: In a glove box, a 25 mL of Schlenk tube equipped with a stir bar was charged with Pd(OAc)2 (0.03 mmol, 0.1 equiv), PCy3 (0.03 or 0.06 mmol, 0.1 or 0.2 equiv), LiOAc (0.45 mmol, 1.5 equiv) (or NaOAc), TEMPO (0.12 mmol, 0.4 equiv), Ag2CO3 (0.9 mmol, 3 equiv). The tube was fitted with a rubber septum and removed out of the glove box. DME (2 mL), propiophenone (0.9 mmol, 3.0 equiv) and thiophene (0.3 mmol, 1.0 equiv) were added in turn to the Schlenk tube through the rubber septum using syringes, and then the septum was replaced with a Teflon screwcap under nitrogen flow (if the thiophene or the substituted propiophenone was solid, it was added to the tube in the glove box). The reaction mixture was stirred at 100 oC or 120 oC for 24 h. After cooling down, the reaction mixture was diluted with 10 mL of ethyl ether, filtered through a pad of silica gel, followed by washing the pad of the silica gel with the same solvent (20 mL), concentrated under reduced pressure. The residue was then purified by flash chromatography on silica gel with 2-15 % ethyl ether in petroleum ether as eluent to provide the corresponding product.

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 1299 - 1303
Angew. Chem.,2013,vol. 125,p. 1337 - 1341,5

36
[ 456-48-4 ]
[ 455-67-4 ]