3-Bromo-5-fluorobenzoic acid → 1-(3-Bromo-5-fluorophenyl)ethan-1-one

HRID 1668735Notes

Reaction equation

HRID 1668735 reaction equation
[CH3:1][Li].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([F:13])[CH:12]=1)[C:7]([OH:9])=O>C(OCC)C>[Br:3][C:4]1[CH:5]=[C:6]([C:7](=[O:9])[CH3:1])[CH:10]=[C:11]([F:13])[CH:12]=1

Participants

4

Reactant 2

HCID 27733393-Bromo-5-fluorobenzoic acidHCID 178418348HCID 178418348, compound

Product 1

HCID 137303591-(3-Bromo-5-fluorophenyl)ethan-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-10 °C

Procedure

Methyllithium (1.3 M in diethyl ether, 35 mL) was added dropwise to 3-bromo-5-fluorobenzoic acid (5 g) in diethyl ether at −78° C. keeping the temperature below −60° C. The reaction was then left to warm to −10° C. and was stirred for 1 h before being carefully quenched with saturated ammonium chloride (100 mL) until pH=3. The product was extracted with diethyl ether (2×100 mL), dried over sodium sulfate and the solvent removed by evaporation to yield 1-(3-bromo-5-fluorophenyl)ethanone as an off-white solid (4.67 g, 94%). 1H NMR (CDCl3): 2.59 (3H, s, ArCOCH3), 7.44 (1H, dd, Ar), 7.59 (1H, dd, Ar), 7.87 (1H, s, Ar).

Workup

  1. customthe temperature below −60° C
  2. waitThe reaction was then left
  3. custombefore being carefully quenched with saturated ammonium chloride (100 mL) until pH=3
  4. extractionThe product was extracted with diethyl ether (2×100 mL)
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-fc05d5bea1dc4726ade6980a9e53d815
Source dataset
uspto-grants-2011_08
Patent number
US07989449B2

Reaction notes

Loading…