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

HRID 2204684Notes

Reaction equation

HRID 2204684 reaction equation
[Br:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:13])[CH:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([O:13][C:4]1[CH:3]=[C:2]([Br:1])[C:11]([CH3:12])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 66611909HCID 66611909, compound

Product 1

HCID 66611339Methyl 2-(acetyloxy)-4-bromo-5-methylbenzoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of methyl 4-bromo-2-hydroxy-5-methylbenzoate (may be prepared as described in Description 14; 1.2 g, 4.90 mmol) in pyridine (10 ml) was added acetic anhydride (2.08 ml, 22.03 mmol). The solution was stirred for one hour, then the solvent was removed in vacuo and purified by column chromatography (SiO2, 6:1 cyclohexane/ethyl acetate) to yield the title compound as a white solid. 1.28 g.

Workup

  1. customthe solvent was removed in vacuo
  2. custompurified by column chromatography (SiO2, 6:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-6b4a6b589167455085cce632b93a7c15
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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