Acetic Anhydride → HCID 66819240, compound

HRID 716011Notes

Reaction equation

HRID 716011 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-ec5616428b17414b9d28a2036e0fb954
Source dataset
uspto-grants-2015_11
Patent number
US09187483B2

Reaction notes

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