1006-33-3|2'-Bromo-5'-fluoroacetophenone| Ambeed

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Quality Control of [ 1006-33-3 ] Purity: 98% SDS Specification

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Product Details of [ 1006-33-3 ]

CAS No. :	1006-33-3
Formula :	C₈H₆BrFO
M.W :	217.04
SMILES Code :	CC(C1=CC(F)=CC=C1Br)=O
MDL No. :	MFCD07780635
InChI Key :	BQXROZQUDCJBBY-UHFFFAOYSA-N
Pubchem ID :	22736080

Safety of [ 1006-33-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 1006-33-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	44.29
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.95
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.21
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.94
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.75

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.04
Solubility	0.2 mg/ml ; 0.000922 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.4
Solubility	0.864 mg/ml ; 0.00398 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.87
Solubility	0.0291 mg/ml ; 0.000134 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.92 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.44

Application In Synthesis of [ 1006-33-3 ]

* 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.

Downstream synthetic route of [ 1006-33-3 ]

[ 1006-33-3 ] Synthesis Path-Downstream 1~35

2
[ 1993-03-9 ]
[ 1006-33-3 ]
[ 705556-87-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium hydroxide; In dichloromethane; at 60℃; for 12h;	A stirred solution of <strong>[1006-33-3]2-bromo-5-fluoroacetophenone</strong> (11.72 g, 54 MMOL) and 2-FLUOROPHENYLBORONIC acid (7.55 g, 54 MMOL) in tetrahydrofuran (600 mL) was treated under nitrogen with [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (ICI) complex with dichloromethane (2.20 g, 2.69 mmol, 5 molepercent) and a 5 N sodium hydroxide solution (21.6 mL, 108 MMOL). The reaction was heated at 60 °C for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent EVAPORATED IN VACUO to a crude brown oil (11.72 g). The crude oil was purified by repetitive, preparative, liquid chromatography on a BIOTAGEE 40 Mi column of pre- packed silica gel (90 g), eluting with a gradient of between 3percent and 10percent methyl TERT- butylether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (10.2 g, 43.9 mmol, 81percent)

References: [1]Patent: WO2004/50631,2004,A1 .Location in patent: Page 94-95.

3
[ 1006-33-3 ]
[ 144025-03-6 ]
[ 705563-34-4 ]

Yield	Reaction Conditions	Operation in experiment
52%	With sodium hydroxide;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 60℃; for 12h;	A stirred solution of <strong>[1006-33-3]2-bromo-5-fluoroacetophenone</strong> (11.72 g, 54 MMOL) and 2, 4-DIFLUOROPHENYLBORONIC acid (8.53 g, 54 MMOL) in tetrahydrofuran (600 mL) was treated under nitrogen with [1, 1APOS;-BIS (DIPHENYLPHOSPHINO) ferrocene] DICHLOROPALLADIUM (II) complex with DICHLOROMETHANE (2.20 g, 2.69 mmol, 5 molepercent) and a 5 N sodium hydroxide solution (21.6 mL, 108 MMOL). The reaction was heated at 60 °C for twelve hours, cooled to room temperature, and the solvent removed in vacuo. The residue was dissolved in diethyl ether, filtered through a short column of silica gel, and the solvent EVAPORATED IN VACUO to a crude brown oil (11.72 g). The crude oil was purified by preparative liquid chromatography on a BIOTAGE 40 Mi column of pre-packed silica gel (90 g), ELUTING with a gradient of between 3percent and 10percent methyl tert-butyl ether in hexane at a flow rate of 50 mL/min to afford, after evaporation of the solvent, the title compound as a purified, colorless oil (7.11 g, 28.4 mmol, 52percent); HRMS [ (+ESI), M/Z] : 251.06705 [M+H] +. Calcd for C14HGF3O : 251.06783 ; IR (FILM), VMAX : 2918,1695, 1604,1481, 1424,1267, 1186,1139, 1100,962, 850,814 CM-1 ; 1H NMR (400 MHz, DMSO-D6) B : 2.44 (s, 3H), 7.16 (tdd, J = 8. 5,2. 5,0. 9 Hz, 1 H), 7.28 (ddd, J = 10. 5,9. 4,2. 6 Hz, 1 H), 7.37-7. 45 (m, 2H), 7.50 (td, J = 8. 5,2. 7 Hz, 1 H), 7.75 (dd, J = 9. 4,2. 7 Hz, 1 H) ; Anal. calcd for C14HGF3O : C, 67.20 ; H, 3.63 ; N, 0.00. Found: C, 67.37 ; H, 3.46 ; N, 0.00.

References: [1]Patent: WO2004/50631,2004,A1 .Location in patent: Page 147-148.

4
[ 313547-14-7 ]
[ 75-16-1 ]
[ 1006-33-3 ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 7509 - 7513.
Angew. Chem.,2013,vol. 125,p. 7657 - 7661,5.
[2]Patent: US2006/25436,2006,A1 .Location in patent: Page/Page column 10.

5
[ 874388-42-8 ]
[ 1006-33-3 ]
[ 874388-43-9 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 90℃; for 14h;	To a solution of 2-([(4-methoxyphenyl)sulfonyl][2-(trimethylsilyl)ethoxy]methyl}amino) phenylboronic acid (3.31 g, 7.57 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.87 g, 0.76 mmol) in dimethoxyethane (30 niL) under argon was added <strong>[1006-33-3]1-(2-bromo-5-fluorophenyl)ethanone</strong> (1.86 g, 8.57 mmol) in ethanol (1 mL). Aqueous sodium carbonate (2 M, 40 mL) was added and the reaction mixture was heated at 90° C. for 14 hours. The solvent was removed in vacuo and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and a saturated, aqueous sodium chloride solution. After drying over anhydrous magnesium sulfate, the organic phase was filtered and the filtrate was evaporated in vacuo to yield the crude title compound as an oil. Purification by silica gel column chromatography by elution with hexane-ethyl acetate (5:1) gave the title compound as a pale yellow oil, which crystallized on standing (2.22 g, 4.19 mmol, 55 percent), m.p. 94-95° C. MS [(ESI), m/z]: 528 [M-H]-; 1H NMR (500 MHz, DMSO-d6) delta7.70 (s, J=7.0 Hz, 1H), 7.64 (d, J=8.9 Hz, 2H), 7.59 (m, 1H), 7.44 (m, 1H), 7.34 (m, 2H), 7.18 (d, J=7.2 Hz, 1H), 7.12 (d, J=8.6 Hz, 2H), 6.92 (d, J=7.6 Hz, 1H), 4.40-4.90 (m, 2H), 3.86 (s, 3H), 3.14 (m, 2H), 2.27 (s, 3H), 0.64 (m, 2H), -0.13 (s, 9H); Anal. calcd for C27H32FNO5SSi: C, 61.22 H, 6.09 N, 2.64. Found: C 61.12, H, 6.01, N 2.44.

References: [1]Patent: US2006/25436,2006,A1 .Location in patent: Page/Page column 15.

6
[ 1006-33-3 ]
[ 1066-54-2 ]
C₁₃H₁₅FOSi [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 2423 - 2432.

7
[ 75-16-1 ]
[ 57381-39-2 ]
[ 1006-33-3 ]

Yield	Reaction Conditions	Operation in experiment
45%		33a 33bTo a solution of 2-bromo-5-fluoro-benzonitrile 33a (10 g, 50 mmol) in dry tetrahydrofuran (100 mL) under nitrogen was added methylmagnesium bromide (3.2 M in ether, 19 mL, 60.0 mmol), and the resulting mixture was heated to reflux for 4 hours. The RM was then cooled down to RT, poured into a 2 N HCl solution (100 mL) and then diluted with methanol (100 mL). The resulting green solution was concentrated on a steam bath for 1 h at which point the organic solvents had been removed and the crude product had precipitated. The reaction mixture was then extracted with ethyl acetate, dried over MgSO4 and concentrated. The residue was purified by column chromatography using heptane and dichloromethane to give 4.88 g (45% yield) of the desired product l-(2-bromo-5-fluorophenyl)ethanone 33b as a pink oil; m/z 218 [M+H]+.
45%	In tetrahydrofuran; diethyl ether; for 4h;Inert atmosphere; Reflux;	To a solution of 2-bromo-5-fluorobenzonitrile (10.0 g, 48.5 mmol) in anhydrous tetrahydrofuran (100 mL) under nitrogen was added methylmagnesium bromide (3.2M in ether, 19 mL, 60.0 mmol). The resulting mixture was heated to reflux for 4 h. The reaction mixture was then cooled, poured into 2N hydrochloric acid (100 mL), and diluted with methanol (100 mL). The organic solvents were removed and the crude product precipitated out. The reaction mixture was extracted with ethyl acetate, dried over MgS04, and concentrated. The residue was purified by column chromatography (heptane/dichloromethane) to give 4.88 g (21.9 mmol, 45percent) of compound 86 as a pink oil.
45%	In tetrahydrofuran; diethyl ether; for 4h;Reflux;	To a solution of 2-bromo-5-fluorobenzonitrile (10.0 g, 48.5 mmol) in anhydrous tetrahydrofuran (100 mL) under nitrogen was added methylmagnesium bromide (3.2M in ether,19 mL, 60.0 mmol). The resulting mixture was heated to reflux for 4 h. The reaction mixture was then cooled, poured into 2N hydrochloric acid (100 mL), and diluted with methanol (100 mL). The organic solvents were removed and the crude product precipitated out. The reaction mixture was extracted with ethyl acetate, dried over MgSO4, and concentrated. The residue was purified by column chromatography (heptane/dichioromethane) to give 4.88 g (21.9 mmol, 45percent)of compound 86 as a pink oil.

References: [1]Patent: WO2010/3658,2010,A1 .Location in patent: Page/Page column 87-88.
[2]Patent: WO2019/86142,2019,A1 .Location in patent: Page/Page column 99.
[3]Patent: WO2019/86141,2019,A1 .Location in patent: Page/Page column 127.

8
[ 1006-33-3 ]
[ 149-73-5 ]
2-bromo-5-fluoro-1-[1-(methoxymethoxy)ethyl]benzene [ No CAS ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 9298 - 9300.

9
[ 1006-33-3 ]
[ 4637-24-5 ]
[ 1246078-71-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 80℃; for 3h;	1.3. Preparation ofl-(2-Bromo-5-fluorophenyl)-3-(dimethylamino)prop-2-en-l-one[0229] A solution of l-(2-bromo-5-fluorophenyl)ethanone (15.7 g, 72.2 mmol) in dimethylformamide dimethyl acetal (24.0 mL, 181 mmol) was heated to 8O0C for 3 h. The reaction mixture was allowed to cool to room temperature and was then cooled to about O0C. Water (100 mL) was slowly added to the reaction mixture while the internal temperature was maintained below about 2O0C. The resulting biphasic mixture was further diluted with MTBE and water. The aqueous phase was extracted with MTBE, and the combined organic phases were washed with water and brine, dried over Na2SO4, and concentrated in vacuo to give l-(2-bromo-5-fluorophenyl)-3-(dimethylamino)prop-2-en- 1-one as a dark orange solid (19.6 g, 100%). This material was used without further purification in the next reaction step. 1H-NMR (500 MHz, CDCl3) delta 7.51 (d, J = 8.8, 4.9 Hz, IH), 7.02-7.12 (m, 2H), 6.93 (dt, J = 8.2, 3.0 Hz, IH), 5.28 (d, J = 12.5 Hz, IH), 3.12 (br s, 3H), 2.89 (s, 3H). Alternatively, a standard aqueous workup was employed to isolate the title compound as a brown oil, which crystallized upon standing (250 g, 96% yield, 97% purity by HPLC).

References: [1]Patent: WO2010/111418,2010,A2 .Location in patent: Page/Page column 99-100.

10
[ 1246078-73-8 ]
[ 1006-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride;Heating;	Example 2 Alternate synthesis of 5-(2-bromo-5-fluorophenyl)-l-ter/-butyl-4-iodo-lH-pyrazole[0235] Readily available 2-bromo-5-fluorobenzoic acid was converted to methyl 3-(2- bromo-5-fluorophenyl)-3-oxopropanoate using condensation with 3-methoxy-3- oxopropanoate. Subsequent de-carboxylation gave l-(2-bromo-5-fluorophenyl)ethanone, which was then converted to 5-(2-bromo-5-fluorophenyl)-l-tert-butyl-4-iodo-lH- pyrazole as described in Example 1.

References: [1]Patent: WO2010/111418,2010,A2 .Location in patent: Page/Page column 102.

11
[ 906673-56-1 ]
[ 1006-33-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trichloroisocyanuric acid; In dichloromethane; at 0.2℃; for 4.5h;	1.2. Preparation ofl-(2-bromo-5-fluorophenyl)ethanone[0228] To a solution of l-(2-bromo-5-fluorophenyl)ethanol (53.4 g, 0.2438 moles) in dichloromethane (500 mL) at 0.20C was added trichloroiso-cyanuric acid (59.5 g, 0.256 moles, 1.05 eq). To the resulting suspension was added TEMPO (2,2,6,6- tetramethylpiperidine 1-oxyl; 188 mg, 1.20 mmol, 0.5 mol%). The reaction mixture was allowed to stir at ice bath temperature until the oxidation was complete (HPLC, about 4.5 h). The resulting reaction mixture was diluted with MTBE (about 1300 mL) and washed with 1 N NaOH (2 x 250 mL), 1 N HCl containing potassium iodide (to remove TEMPO; 8 g KI in 1000 mL 1 N HCl; 2 x 250 mL), 1 N NaHCO3 containing sodium thiosulfate (to remove I2; 15 g Na2S2O3 in 1000 mL 1 N NaHCO3), 1 N HCl containing potassium iodide (1 x 200 mL), 1 N NaHCO3 containing sodium thiosulfate (2 x 200 mL), and brine (150 mL). After drying (anhydrous MgSO4), the solvent was removed at reduced pressure to give l-(2-bromo-5-fluorophenyl)ethanone as a pale amber liquid (52.96g, about 97 %) in 98% purity by HPLC, which was used in the next step without further purification. 1H- NMR (300 MHz, CDCl3) delta 7.59 (dd, J = 8.7, 4.9 Hz, IH), 7.19 (dd, J = 8.5, 3.0 Hz, IH), 7.04 (ddd, J = 9.1, 7.8, 3.0 Hz, IH), 2.64 (s, 3H).
	With manganese(IV) oxide; In dichloromethane; for 12h;Reflux;	General procedure: Before evacuated and recharged with N2 for 3 times, 2-bromobenzaldehyde derivative (5 mmol) was added to the tube. THF (20 mL) was added to the tube and the mixture was cooled to -78 oC. MeMgCl (1.5-2 eq.) was dropwised to the mixture. The reaction was performed for 1 h at -78 oC, 1 h at 0 oC. 10 mL 2N HCl and 20 mL water were added to the tube and the mixture was extracted with Et2O (10 mL x 3), dried by anhydrous Na2SO4. Evaporation of the solvent followed by purification on silica gel provided 1-(2-bromophenyl)ethanol derivative. 1-(2-bromophenyl)ethanol derivative (3 mmol) and 10 mL CH2Cl2 were added to a 25 mL round-bottom flask. After MnO2 (10 eq., 30 mmol) was added to the mixture slowly, the reaction was heated to reflux for 12 h. After filtration and purification on silica gel, 1-(2-bromophenyl)ethanone derivative was provided, yield 60-84%.
	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 2h;	General procedure: To a solution of 2-bromo-4-fluorobenzaldehyde (1.0 g, 5.0 mmol, 1.0 equiv.) in dry ether (10 mL, 0.5 M) at 0 C was added dropwise a solution of methylmagnesium bromide in Et2O (10 mmol, 2.0 equiv.) under N2 atmosphere. The resulting reaction mixture was stirred at 0 C for 3 hours, then quenched with saturated aqueous NH4Cl solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the corresponding 1- (2-bromo-4-fluorophenyl)ethan-1-ol. To a solution of 1-(2-bromo-4-fluorophenyl)e- than-1-ol (1.0 equiv.) in dry CH2Cl2 (0.2 M) was added a homogeneous mixture of pyridinium chlorochromate (PCC, 3.2 g, 15 mmol, 3.0 equiv.) and silica gel (3.2 g, 1:1 by mass). The resulting suspension was stirred at room temperature for 2 hours, then filtered through a pad of silica gel, washed with CH2Cl2 and concentrated in vacuo. The crude product was used for the next step without further purification. From 1-(2- bromo-4-fluorophenyl)ethan-1-one, the corresponding benzamide was synthesized by the same method of 1a.

References: [1]Patent: WO2010/111418,2010,A2 .Location in patent: Page/Page column 99.
[2]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7836 - 7848.
[3]Journal of Organic Chemistry,2017,vol. 82,p. 11585 - 11593.
[4]Organic Letters,2012,vol. 14,p. 3230 - 3232.
[5]Journal of the American Chemical Society,2014,vol. 136,p. 16748 - 16751.
[6]Organic Letters,2015,vol. 17,p. 5566 - 5569.
[7]Chinese Chemical Letters,2015,vol. 26,p. 1231 - 1235.
[8]Tetrahedron Letters,2017,vol. 58,p. 285 - 288.
[9]Chemistry - An Asian Journal,2018,vol. 13,p. 1897 - 1901.

12
[ 1006-33-3 ]
[ 1326778-77-1 ]

References: [1]Chemical Communications,2011,vol. 47,p. 8976 - 8978.

13
[ 1006-33-3 ]
[ 1326778-65-7 ]

References: [1]Chemical Communications,2011,vol. 47,p. 8976 - 8978.

14
[ 1006-33-3 ]
[ 1326778-66-8 ]

References: [1]Chemical Communications,2011,vol. 47,p. 8976 - 8978.

15
[ 627-19-0 ]
[ 1006-33-3 ]
[ 1350844-26-6 ]

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7836 - 7848.

16
[ 1006-33-3 ]
[ 1350845-13-4 ]
7-fluoro-3-propylisoquinolin-1-amine [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7836 - 7848.

17
[ 94569-84-3 ]
[ 1006-33-3 ]

References: [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7836 - 7848.
[2]Journal of the American Chemical Society,2014,vol. 136,p. 16748 - 16751.
[3]Chinese Chemical Letters,2015,vol. 26,p. 1231 - 1235.
[4]Tetrahedron Letters,2017,vol. 58,p. 285 - 288.
[5]Journal of Organic Chemistry,2017,vol. 82,p. 11585 - 11593.
[6]Chemistry - An Asian Journal,2018,vol. 13,p. 1897 - 1901.

18
[ 1006-33-3 ]
[ 100-52-7 ]
1-(2-bromo-5-fluorophenyl)-3-phenylprop-2-en-1-one [ No CAS ]

References: [1]European Journal of Organic Chemistry,2012,p. 3001 - 3008.

19
[ 1006-33-3 ]
[ 100-52-7 ]
[ 1380424-26-9 ]

References: [1]European Journal of Organic Chemistry,2012,p. 3001 - 3008.

20
[ 1006-33-3 ]
[ 532-96-7 ]
[ 1374227-76-5 ]

References: [1]Organic Letters,2012,vol. 14,p. 2552 - 2555.

21
[ 1006-33-3 ]
[ 1379534-62-9 ]

References: [1]Organic Letters,2012,vol. 14,p. 3230 - 3232.

22
[ 1006-33-3 ]
C₁₄H₂₃FSi₂ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 3230 - 3232.

23
[ 1006-33-3 ]
C₁₆H₂₃Cl₂FOSi₂ [ No CAS ]

References: [1]Organic Letters,2012,vol. 14,p. 3230 - 3232.

24
[ 1006-33-3 ]
[ 1379534-72-1 ]

References: [1]Organic Letters,2012,vol. 14,p. 3230 - 3232.

25
[ 1006-33-3 ]
[ 2065-66-9 ]
1-bromo-4-fluoro-2-(prop-1-en-2-yl)benzene [ No CAS ]