Sulfuric Acid → 3-Bromo-4-hydroxybenzamide

HRID 228410

Reaction equation

HRID 228410 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].[OH:11]S(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]([NH2:6])=[O:11]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 753413-Bromo-4-hydroxybenzonitrile

Product 1

HCID 151699323-Bromo-4-hydroxybenzamideYield 83%

Conditions

Temperature
80 °C

Procedure

3-Bromo-4-hydroxy-benzonitrile (495 mg, 2.5 mmol) is dissolved in H2SO4 98%, heat the solution at 80° C. for 1 hour. Cool the mixture at room temperature and pour it into ice-water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4. Eliminate the solvent to obtain the title compound (450 mg, 83%). 1H-NMR (metanol-d4, 200 MHz): 8.04 (d, 1H, J=2.0 Hz), 7.70 (dd, 1H, J=2.0 and 8.4 Hz), 6.93 (d, 1H, J=8.6 Hz)

Workup

  1. temperatureCool the mixture at room temperature
  2. extractionExtract the aqueous layer with EtOAc
  3. dry with materialDry the organic layer over Na2SO4

Sources & evidence

ORD record
ord-6bcd3c0f6b7f4f56ab4d24db404d32c0
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Linked notes

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