Acetic Anhydride → 4-Bromo-2-fluorophenethyl acetate

HRID 1525879Notes

Reaction equation

HRID 1525879 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([F:11])[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>ClCCl.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:12]([O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:11])(=[O:14])[CH3:13]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 536606944-Bromo-2-fluorobenzeneethanol

Product 1

HCID 712711174-Bromo-2-fluorophenethyl acetateYield 90.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(4-bromo-2-fluorophenyl)ethanol (3.01 mmol) in dichloromethane (5 mL) and pyridine (10 mL) was treated with 4-(dimethylamino)pyridine (0.151 mmol) and acetic anhydride (9.04 mmol). The reaction was stirred overnight at room temperature. At this point the reaction was diluted with dichloromethane (100 mL). The organic layer was washed three times with 1N aq HCl, once with saturated aq sodium bicarbonate, and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a pale beige oil (710 mg, 81% yield). 1H NMR (400 MHz, DMSO-d6) d ppm 1.96 (s, 3 H) 2.90 (t, J=6.44 Hz, 2 H) 4.20 (t, J=6.57 Hz, 2 H) 7.26-7.43 (m, 2 H) 7.51 (dd, J=9.73, 1.89 Hz, 1 H).

Workup

  1. washThe organic layer was washed three times with 1N aq HCl
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bcd694fadea24b7a842dc9c9bac530f6
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

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