t-Butyl bromide → Tert-butyl 4-bromobenzoate

HRID 735869Notes

Reaction equation

HRID 735869 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11](Br)([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[C:11]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 10485t-Butyl bromideHCID 114644-Bromobenzoic acid

Product 1

HCID 11334366Tert-butyl 4-bromobenzoate

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-bromobenzoic acid (100 g, 0.5 mol) in dry CH2Cl2 (1.5 L) was added silver carbonate (275 g, 1 mol) and molecular sieves (4A, 100 g). The reaction mixture was cooled to 0° C. and then tert-butyl bromide (115 mL) was added dropwise over a period of 45 min. The reaction mixture was allowed to stir at Rt for 20 h and filtered off the solid. The filtrate was washed with an aqueous solution of NaHCO3 (10%), water, brine and dried. The solvent was removed under vacuum to the title compound (100 g, 79%) as colorless liquid.

Workup

  1. filtrationfiltered off the solid
  2. washThe filtrate was washed with an aqueous solution of NaHCO3 (10%), water, brine
  3. customdried
  4. customThe solvent was removed under vacuum to the title compound (100 g, 79%) as colorless liquid

Sources & evidence

ORD record
ord-32bd49907c734105978a79f3bc794c04
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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