Isobutylene → Tert-butyl 4-bromobenzoate

HRID 735860Notes

Reaction equation

HRID 735860 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.FC(F)(F)S(O)(=O)=O.[CH3:19][C:20](=[CH2:22])[CH3:21]>ClCCl>[C:20]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:22])([CH3:21])[CH3:19]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 114644-Bromobenzoic acidHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 11334366Tert-butyl 4-bromobenzoateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-bromobenzoic acid (100 g, 0.5 mol), trifluoromethane sulphonic acid (2.6 mL, 0.03 mol) and isobutylene (1.5 L) in dichloromethane (1.5 L) was stirred at RT in a closed autoclave for 5 days. The organic layer was washed with an aqueous solution of NaHCO3 (10%), water, brine, dried and concentrated to give tert-butyl-4-bromobenzoate (90 g, 71%).

Workup

  1. washThe organic layer was washed with an aqueous solution of NaHCO3 (10%), water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a4859eed516943b89bc055610c9010fb
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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