Sodium Carbonate → Tert-butyl-3-(4-tolyl)benzoate

HRID 735844Notes

Reaction equation

HRID 735844 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH3:24])[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:18]2[CH:19]=[CH:20][C:15]([CH3:24])=[CH:16][CH:17]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 334079tert-Butyl 3-bromobenzoate

Product 1

HCID 18398672Tert-butyl-3-(4-tolyl)benzoateYield 92.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of tert-butyl-3-bromobenzoate (65 g, 0.25 mol), 4-tolyl boronic acid (41.3 g, 0.30 mol) and sodium carbonate (150 g) in a mixture of toluene (500 mL) and water (50 mL), tetrakis-triphenylphosphine palladium(0) (14.5 g, 0.05 mol) was added and the reaction mixture was refluxed overnight. Cooled to RT, toluene layer was separated. The organic layer was washed with water, brine, dried. The solvent was removed under vacuum to give tert-butyl-3-(4-tolyl)benzoate (62 g, 90%).

Workup

  1. additionwas added
  2. temperaturethe reaction mixture was refluxed overnight
  3. customtoluene layer was separated
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5a6c6b5c89a1484e8538f88bfdd5393e
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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