Hydrochloric Acid → Methyl 2-(2-bromophenyl)acetate

HRID 354267Notes

Reaction equation

HRID 354267 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=[O:11].[CH3:13]O>>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[Br:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 877542-Bromophenylacetic acid

Product 1

HCID 8063364Methyl 2-(2-bromophenyl)acetate

Procedure

Hydrochloric acid (gas) was bubbled through 15.8 g (73.5 mmol) 2-bromophenylacetic acid in 100 mL of methanol for 10 min. The resulting solution was partitioned between 100 mL water and 100 mL CH2Cl. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure to give 16.8 g (73.5 mmol) of methyl-2-bromophenylacetate which was combined with 9.0 g (80.8 mmol) of 1-vinyl-2-pyrrolidinone, and 100 mL of dry THF under argon in a 250 mL round-bottomed flask.

Workup

  1. customThe resulting solution was partitioned between 100 mL water and 100 mL CH2Cl
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b9d6f2658b774874af8d1ecd75ca469c
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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