Acetic Anhydride → 4-Acetoxy-2-fluorobenzoic acid

HRID 2237363Notes

Reaction equation

HRID 2237363 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:19]([O:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:10]=1)(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 27833982-Fluoro-4-hydroxybenzoic Acid

Product 1

HCID 227214164-Acetoxy-2-fluorobenzoic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred mixture of 2-fluoro-4-hydroxybenzoic acid (5 g) (G. W. Gray et al. Mol. Cryst. Liq. Cryst. 67, 1981, 1-24), 4-dimethylaminopyridine (0.010 g) and triethylamine (11 mL) in DCM (100 mL) was treated with acetic anhydride (6.35 mL). After 2 h the solution was evaporated and the residue redissolved in EtOAc, washed with 5% citric acid, water (3×), dried (Na2SO4) and evaporated to give the title compound as a white solid (4.92 g); APCI m/z 199.1 [M+H]+.

Workup

  1. customAfter 2 h the solution was evaporated
  2. dissolutionthe residue redissolved in EtOAc
  3. washwashed with 5% citric acid, water (3×)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c4012973f22e4bbbb1c0fd9bcb055669
Source dataset
uspto-grants-2010_05
Patent number
US07718621B2

Reaction notes

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