Toluene → t-butyl 3-bromo-4-methylbenzoate

HRID 1953756Notes

Reaction equation

HRID 1953756 reaction equation
COC(OC)N(C)C.[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([OH:15])=[O:14].[C:20]1([CH3:26])[CH:25]=CC=C[CH:21]=1>>[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:13]([O:15][C:20]([CH3:26])([CH3:25])[CH3:21])=[O:14]

Participants

4

Reactant 3

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 821303-Bromo-4-methylbenzoic acid

Product 1

HCID 12051722t-butyl 3-bromo-4-methylbenzoateYield 69%

Conditions

Temperature
75 °C

Procedure

Dimethylformamide dimethyl acetal (48 mL, 200 mmol) was added dropwise over 15 min to a suspension of 3-bromo-4-methylbenzoic acid (85%; 10.75 g, 42.5 mmol) in toluene (100 mL) at 70° C. The reaction was stirred at 70-80° C. for an additional 0.5 h, then was cooled, washed sequentially with water and 5% sodium bicarbonate, and dried (sodium sulfate). The mixture was filtered through a pad of silica gel, and the filter pad was washed with toluene. The filtrate was concentrated to afford the title compound (8.0 g, 69%) as a yellow oil. TLC (toluene) Rf 0.68.

Workup

  1. temperaturewas cooled
  2. washwashed sequentially with water and 5% sodium bicarbonate
  3. dry with materialdried (sodium sulfate)
  4. filtrationThe mixture was filtered through a pad of silica gel
  5. washthe filter pad was washed with toluene
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6e247d8ee4464190b41b9a80fe92eab5
Source dataset
uspto-grants-2000_09
Patent number
US06117866

Reaction notes

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