t-Butyl bromide → tert-Butyl 3-bromobenzoate

HRID 735843Notes

Reaction equation

HRID 735843 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11](Br)([CH3:14])([CH3:13])[CH3:12]>C(=O)([O-])[O-].[Ag+2]>[C:11]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 10485t-Butyl bromideHCID 114563-Bromobenzoic acid

Product 1

HCID 334079tert-Butyl 3-bromobenzoateYield 57%

Reagents, catalysts & solvents 1

HCID 178418647HCID 178418647, compoundCatalyst

Procedure

To a mixture of 3-bromo benzoic acid (10 g, 0.5 mol), silver carbonate (276 g, 1 mol) and dry molecular sieves (100 g) taken in dry CH2Cl2 (2 L), tert-butylbromide (115 mL, 1 mol) was added dropwise at 0° C. and the reaction mixture was stirred overnight at RT. The solid was filtered and washed with dichloromethane. Organic layer was washed with 10% aqueous solution of NaHCO3 (2×500 mL), water (2×500 mL), brine and dried. The solvent was removed under vacuum to give tert-butyl-3-bromobenzoate (70 g, 57%).

Workup

  1. customdry molecular sieves (100 g)
  2. filtrationThe solid was filtered
  3. washwashed with dichloromethane
  4. washOrganic layer was washed with 10% aqueous solution of NaHCO3 (2×500 mL), water (2×500 mL), brine
  5. customdried
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e494cf4ae149400caefb404d731b0edd
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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