Thionyl Chloride → HCID 86640660, compound

HRID 558129Notes

Reaction equation

HRID 558129 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH2:13][C:14]([OH:16])=O>C(Cl)Cl>[Br:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH2:13][C:14]([Cl:3])=[O:16]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 34778092-Bromo-4-fluorophenylacetic acid

Product 1

HCID 86640660HCID 86640660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add thionyl chloride (1.5 g, 12.6 mmol) to a solution of (2-bromo-4-fluoro-phenyl)-acetic acid (0.3 g, 1.26 mmol) in DCM (3 mL). Reflux the mixture for 2 h. Remove the solvent and excess thionyl chloride under reduced pressure to give the intermediate (2-bromo-4-fluorophenyl)-acetyl chloride. Dissolve the residue in DCM (3 mL) and add to a stirred solution of ethanolamine (0.15 mL, 2.52 mmol) in DCM (3 mL) at 0° C. Stir the mixture overnight. Dilute with DCM and wash with saturated NaHCO3, water, and aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo to give the title compound as a white solid (300 mg, 86%). MS (ES) m/z 276 [M+1]+.

Workup

  1. temperatureReflux the mixture for 2 h
  2. customRemove the solvent and excess thionyl chloride under reduced pressure

Sources & evidence

ORD record
ord-784c7bef2a9a4f0a9c79f5e26f72914c
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

Loading…