tert-Butanol → tert-butyl 2-(2-bromophenyl)acetate

HRID 2248277Notes

Reaction equation

HRID 2248277 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].N1(C2C=CN=CC=2)CCCC1.[C:23](O)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:10]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 755674-PyrrolidinopyridineHCID 877542-Bromophenylacetic acid

Product 1

HCID 14371760tert-butyl 2-(2-bromophenyl)acetateYield 8.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromophenylacetic acid (5.02 g), N,N-dicyclohexylcarbodiimide (5.3 g), 4-pyrrolidinopyridine (0.4 g) and t-butanol (1.74 g) in DCM (120 ml) was stirred at room temperature, under nitrogen, for 4 h. The mixture was left to stand for 18 h, then ER (150 ml) was added and the mixture was filtered and washed with ER. The filtrate was evaporated in vacuo to leave a yellow suspension. F.C.C. (A) eluting with hexane gave a white semisolid, which was further chromatographed eluting with hexane, then 1% ER in hexane, and finally 2% gave a colorless liquid. Vacuum distillation by Kugelrohr at 0.4 mmHg and at 140°-150° gave the title compound as a colorless oil (0.55 g). T.l.c. (A) hexane:ER (3:1) Rf 0.68.

Workup

  1. waitThe mixture was left
  2. waitto stand for 18 h
  3. additionER (150 ml) was added
  4. filtrationthe mixture was filtered
  5. washwashed with ER
  6. customThe filtrate was evaporated in vacuo
  7. customto leave a yellow suspension
  8. wash(A) eluting with hexane
  9. customgave a white semisolid, which
  10. customwas further chromatographed
  11. washeluting with hexane
  12. custom1% ER in hexane, and finally 2% gave a colorless liquid
  13. distillationVacuum distillation by Kugelrohr at 0.4 mmHg

Sources & evidence

ORD record
ord-c6ce1d2f42524075a4e0260bb61a56c5
Source dataset
uspto-grants-1991_08
Patent number
US05039673

Reaction notes

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