Acetic Anhydride → HCID 66819240, compound

HRID 84957Notes

Reaction equation

HRID 84957 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:12][C:9]1[CH:10]=[CH:11][C:2]([Br:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 189336882-broMo-5-hydroxybenzoic acid Methyl ester

Product 1

HCID 66819240HCID 66819240, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To methyl 2-bromo-5-hydroxybenzoate (20 g, 87 mmol) in pyridine (100 mL) was added acetic anhydride (10.2 g, 100 mmol) at 0° C. The mixture was stirred at ambient temperature for 16 hours, concentrated, and ethyl acetate was added. The mixture was washed with saturated NH4Cl(aq) to afford the crude title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.79 (d, J=8.7 Hz, 1H), 7.58 (d, J=2.8 Hz, 1H), 7.30 (dd, J=8.7, 2.8 Hz, 1H), 3.86 (s, 3H), and 2.28 (s, 3H).

Workup

  1. concentrationconcentrated
  2. additionethyl acetate was added
  3. washThe mixture was washed with saturated NH4Cl(aq)

Sources & evidence

ORD record
ord-07250d3db8c54b86a2fa1ed88b5f77ec
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

Loading…