Methanol → Methyl (4-bromo-2-fluorophenyl)acetate

HRID 72969Notes

Reaction equation

HRID 72969 reaction equation
C[Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[C:11]([F:19])[CH:10]=1.[CH3:20]O>C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([O:18][CH3:20])=[O:17])=[C:11]([F:19])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 140537922-(4-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 53429406Methyl (4-bromo-2-fluorophenyl)acetateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trimethylsilyl diazomethane (11.6 mL of 2 M in toluene, 23.2 mmol) was added dropwise to a solution of 2-(4-bromo-2-fluoro-phenyl)acetic acid (4.5 g, 19.3 mmol) in a mixture of toluene (7.65 mL)/methanol (7.65 mL) under a nitrogen atmosphere at room temperature. The reaction mixture was then quenched with a few drops of acetic acid and the solvents were concentrated in vacuo. The residue was purified by silica gel column chromatography using 0-10% EtOAc-hexanes as eluent to yield methyl 2-(4-bromo-2-fluoro-phenyl)acetate (4.3 g, 91%). 1H NMR (400 MHz, CDCl3) δ 7.28-7.22 (m, 2H), 7.15 (t, J=8.0 Hz, 1H), 3.71 (s, 3H), 3.63 (d, J=1.0 Hz, 2H).

Workup

  1. customThe reaction mixture was then quenched with a few drops of acetic acid
  2. concentrationthe solvents were concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4b5f8c4b356943fb930a8e94e3e59f08
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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