Methanol → methyl 2-(5-bromo-2-fluorophenyl)acetate

HRID 216210Notes

Reaction equation

HRID 216210 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1.S(=O)(=O)(O)O.[CH3:18]O>>[CH3:18][O:10][C:9](=[O:11])[CH2:8][C:6]1[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 35846902-(5-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 58148958methyl 2-(5-bromo-2-fluorophenyl)acetate

Conditions

Temperature
64 °C

Procedure

To a solution of 5-bromo-2-fluorophenylacetic acid (5 g) in MeOH (200 mL) is added concentrated sulfuric acid (2 mL) and the solution is heated at 64° C. for 16 hours. The solution is evaporated in vacuo and the residue is taken up in EtOAc and washed with 10% sodium bicarbonate, brine and dried over sodium sulfate. The solution is filtered and evaporated in vacuo to afford (5-bromo-2-fluoro-phenyl)-acetic acid methyl ester (5.1 g). 1H NMR (300 MHz, CDCl3) □7.3-7.5 (m, 2H); 6.9 (m, 1H); 3.9 (s, 3H).

Workup

  1. customThe solution is evaporated in vacuo
  2. washwashed with 10% sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution is filtered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9e574eeed79d45da9a30ccfbae9d5b6c
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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