Thionyl Chloride → 4-Bromo-2-fluorobenzoyl chloride

HRID 911287Notes

Reaction equation

HRID 911287 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([F:11])[CH:3]=1.S(Cl)([Cl:14])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:14])=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 27340264-Bromo-2-fluorobenzoyl chlorideYield 15,369.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Combine 4-bromo-2-fluoro-benzoic acid (5.0 g, 22.83 mmol), thionyl chloride (10 mL, 0.137 mmol) in toluene (10 mL) and reflux for 2 h. Evaporate the reaction mixture to obtain 4-bromo-2-fluoro-benzoyl chloride (5.0 g, 93%) and use for the next step without further purification. Dissolve tert-butylamine (0.8 mL, 5.12 mmol) and triethylamine (0.8 mL, 6.32 mmol) in anhydrous DCM (20 mL), cool to 0° C. and add a solution of 4-bromo-2-fluoro-benzoyl chloride (1.0 g, 4.22 mmol) in anhydrous DCM (10 mL). Stir the reaction mixture at 0° C. for 10 min, warm to ambient temperature and continue to stir for 30 min. Wash the reaction mixture with brine (2×10 mL), dry the organic extracts over anhydrous Na2SO4, evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the desired intermediate as a white solid (1.0 g, 87%). MS (ES+) m/z: 275 (M+H)+.

Workup

  1. customEvaporate the reaction mixture

Sources & evidence

ORD record
ord-68a17bda86b94dc49e681273753ebd3c
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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