Acetic Anhydride → Methyl 2-(acetyloxy)-5-bromo-4-methylbenzoate

HRID 2204674Notes

Reaction equation

HRID 2204674 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Br:8][C:9]1[C:10]([CH3:20])=[CH:11][C:12]([OH:19])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15]>N1C=CC=CC=1>[C:1]([O:19][C:12]1[CH:11]=[C:10]([CH3:20])[C:9]([Br:8])=[CH:18][C:13]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11425090Methyl 5-bromo-2-hydroxy-4-methylbenzoate

Product 1

HCID 66611776Methyl 2-(acetyloxy)-5-bromo-4-methylbenzoateYield 97.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (3.06 mL, 32.5 mmol) was added to a solution of methyl 5-bromo-2-hydroxy-4-methylbenzoate (3.98 g, 16.24 mmol), which may be prepared according to procedure described in Description 2, in Pyridine (10 mL) was added. The reaction mixture was stirred for four hours. The solvent was removed in vacuo and the residue was purified by SP4 (10-20% EtOAc/hexane) to yield the desired compound as oil (4.54 g, 97% yield).

Workup

  1. custommay be prepared
  2. additionwas added
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by SP4 (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-4ab2132f0ff043b6be208555c30c74cf
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

Loading…