Trimethyl orthoformate → Methyl 2-(3-bromophenyl)acetate

HRID 1455204Notes

Reaction equation

HRID 1455204 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH:12](OC)(OC)OC>CO.C1(C)C=CC=CC=1>[CH3:12][O:10][C:9](=[O:11])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 9005Trimethyl orthoformateHCID 74653(3-Bromophenyl)acetic acid

Product 1

HCID 11746402Methyl 2-(3-bromophenyl)acetateYield 100.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of (3-bromo-phenyl)-acetic acid (10.4 g, 48.5 mmol), in methanol (80 mL), was treated with trimethyl orthoformate (6.5 mL, 59.4 mmol). HCl gas was bubbled through the stirred solution for 10 minutes. The HCl addition was exothermic. After stirring for 15 minutes HPLC analysis of the solution showed complete conversion to product. After stirring for 16 hrs at ambient temperature the solution was diluted with toluene (100 mL) and concentrated under reduced pressure to afford a biphasic mixture. This liquid was diluted with toluene and concentrated under reduced pressure to afford (3-bromo-phenyl)-acetic acid methyl ester (11.2 g, quantitative yield) as a pale yellow liquid. 1H-NMR (400 MHz, CDCl3): δ 7.46-7.38 (2H, m), 7.23-7.18 (2H, m), 3.71 (3H, m), 3.60 (2H, m).

Workup

  1. customHCl gas was bubbled through the stirred solution for 10 minutes
  2. additionThe HCl addition
  3. stirringAfter stirring for 16 hrs at ambient temperature the solution
  4. additionwas diluted with toluene (100 mL)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a biphasic mixture
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b996bb37a3f04cf69c3abd8f5f3889b2
Source dataset
uspto-grants-2009_01
Patent number
US07482366B2

Reaction notes

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