Pyridine → 4-Bromo-2-fluorophenyl acetate

HRID 38997

Reaction equation

HRID 38997 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11].N1C=CC=CC=1>>[C:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:9])(=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 226485254-Bromo-2-fluorophenyl acetateYield 83%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-fluorophenol (5 g, 30 mmol) and acetic anhydride (13.4 g, 130 mmol) in pyridine (10.6 ml, 130 mmol) was heated at 100° C. for 3 h and then brought to ambient temperature and poured into water. HCl (1 N and 6 N) was added and the solution was extracted with EtOAc. The combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml), dried (Na2SO4) and evaporated to dryness to give the title compound (5.8 g). MS m/z (rel. intensity, 70 eV) 233 (M+, 11), 232 (M+, 12), 191 (95), 190 (bp), 161 (8).

Workup

  1. custombrought to ambient temperature
  2. additionwas added
  3. extractionthe solution was extracted with EtOAc
  4. washThe combined organic phases were washed with sodium bicarbonate (saturated, 3×50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0ee4864d93714b428fe4be10c94032b6
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Linked notes

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