Water → tert-butyl 2-(4-bromophenyl)acetate

HRID 545454Notes

Reaction equation

HRID 545454 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.O.[C:22](OC(C)=O)([CH3:25])([CH3:24])[CH3:23]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8000Boron trifluoride etherateHCID 10908tert-Butyl acetateHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 14775457tert-butyl 2-(4-bromophenyl)acetate

Procedure

To a solution of 4-bromophenylacetic acid (5.00 g, 23.2 mmol) in tBuOAc (75 mL) was added BF3.OEt2 (2.95 mL, 23.2 mmol). The mixture was allowed to stir overnight at room temperature and poured into H2O. The aqueous phase was extracted with EtOAc. The organic phase was washed with sat. aq NaHCO3, dried over anhydrous Na2SO4, and concentrated in vacuo. Purification by flash chromatography on silica gel (0% to 100% EtOAc in hexanes) provided the title compound. 1H NMR (500 MHz, CDCl3): δ 7.48 (d, J=8.0 Hz, 2 H), 7.19 (d, J=8.0 Hz, 2 H), 3.52 (s, 2 H), 1.48 (s, 9 H).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc
  2. washThe organic phase was washed with sat. aq NaHCO3
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel (0% to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-33e8eddae4f44679b6271562d3073c7a
Source dataset
uspto-grants-2011_05
Patent number
US07935713B2

Reaction notes

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