Acetic Anhydride → Phenol, 2-fluoro-, acetate

HRID 1786822Notes

Reaction equation

HRID 1786822 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15].[OH-].[Na+]>>[C:1]([O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[F:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 97072-FluorophenolHCID 14798Sodium Hydroxide

Product 1

HCID 141495Phenol, 2-fluoro-, acetateYield 103%

Procedure

Acetic anhydride (81 cm3, 856 mmol) was added dropwise to a stirred mixture of 2-fluorophenol (60.0 g, 535 mmol) and aqueous sodium hydroxide (4 N, 214 cm3, 856 mmol) at 0° C. After the reaction had been stirred for 30 min the aqueous layer was separated from the organic portion and washed with dichloromethane (150 cm3). The combined organic extracts were washed with aqueous sodium hydroxide solution (4 N, 150 cm3) and then brine (100 cm3). The organic phase was dried (Na2SO4) and the solvent was evaporated in vacuo to afford the title compound (84.9 g, >100%).

Workup

  1. customwas separated from the organic portion
  2. washwashed with dichloromethane (150 cm3)
  3. washThe combined organic extracts were washed with aqueous sodium hydroxide solution (4 N, 150 cm3)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-457595687ac04347a558c4b2ae8c9ef7
Source dataset
uspto-grants-2009_03
Patent number
US07507824B2

Reaction notes

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