tert-Butyl acetate → Tert-butyl 4-bromo-3-methylbenzoate

HRID 576249Notes

Reaction equation

HRID 576249 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10]C(C(OC)=O)=[CH:4][C:3]=1[CH3:12].[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:14]([C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 3

HCID 10908tert-Butyl acetate2×HCID 3294148Methyl 4-bromo-3-methylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 4-bromo-3-methylbenzoate (4.85 g) and tert-butyl acetate (3 mL) was added 1M potassium tert-butoxide in THF (0.3 mL). The mixture was stirred under vacuum for 10 minutes and treated with another equivalent of tert-butyl acetate and 1 mol % of (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) dichloromethane. This procedure was repeated three times. The mixture was diluted with ethyl acetate (40 mL) and washed with 5% aqueous HCl, water and brine. After drying over Na2SO4, the mixture was concentrated.

Workup

  1. washwashed with 5% aqueous HCl, water and brine
  2. dry with materialAfter drying over Na2SO4
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-807e665a0e744a4ab222c21552d484e8
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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