Acetic Anhydride → Methyl 6-(acetyloxy)-3-bromo-2-methylbenzoate

HRID 1247456Notes

Reaction equation

HRID 1247456 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([OH:12])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14](OC(=O)C)(=[O:16])[CH3:15]>N1C=CC=CC=1>[C:14]([O:12][C:9]1[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([CH3:13])[C:2]([Br:1])=[CH:11][CH:10]=1)(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 21907510HCID 21907510, compound

Product 1

HCID 21907498Methyl 6-(acetyloxy)-3-bromo-2-methylbenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of Example 106B (1.05 g, 4.3 mmol) in pyridine (3 mL) was treated with acetic anhydride (0.82 mL, 8.6 mmol), stirred at room temperature for 2 hours, and partitioned between ethyl acetate and 2N HCl. The organic phase was washed sequentially with aqueous NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated to give 1.19 g (97% yield) of the desired product. MS (ESI(+)) m/e 304, 306 (M+H)+.

Workup

  1. custompartitioned between ethyl acetate and 2N HCl
  2. washThe organic phase was washed sequentially with aqueous NaHCO3, water, and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d2bea2dd5c64e7892d9728472c51cdb
Source dataset
uspto-grants-2006_10
Patent number
US07129260B2

Reaction notes

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