Tert-butyl 4-bromo-3-methylbenzoate → Tert-butyl 3-methylbenzoate

HRID 968871Notes

Reaction equation

HRID 968871 reaction equation
[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10](Br)=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.CO.[Pd]>[C:1]([O:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:14])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 11845988Tert-butyl 4-bromo-3-methylbenzoate

Product 1

HCID 236097Tert-butyl 3-methylbenzoateYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

4-Bromo-3-methyl-benzoic acid tert-butyl ester (0.39 g, 1.438 mmol) was hydrogenated over 10% Pd—C (0.5 g) under H2 (50 psi) in EtOAc—MeOH (4:1, 20 mL) for 5 h. After filtration through Celite, filtrate was evaporated to dryness. Yield: 97%. MS (ESI) 193.28 (M+H+).

Workup

  1. filtrationAfter filtration through Celite, filtrate
  2. customwas evaporated to dryness

Sources & evidence

ORD record
ord-f327d32dbfcf40f8b6a78ba329312724
Source dataset
uspto-grants-2007_12
Patent number
US07304085B2

Reaction notes

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