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

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

Reactant 4

HCID 962Water

HCID 8000Boron trifluoride etherate

HCID 10908tert-Butyl acetate

HCID 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).