Water → Benzamide, N-(2,6-dimethylphenyl)-4-hydroxy-

HRID 2165124Notes

Reaction equation

HRID 2165124 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:19])[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 178983Benzamide, N-(2,6-dimethylphenyl)-4-methoxy-

Product 1

HCID 10633847Benzamide, N-(2,6-dimethylphenyl)-4-hydroxy-Yield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

A solution of 6.4 g of N-(2,6-dimethylphenyl)-4-methoxybenzamide in methylene chloride was cooled to -75° C. Boron tribromide (25 g) was added over a 15 minute period. The reaction mixture was allowed to warm over 2 hours and then heated at reflux for 2 hours. The reaction was again cooled to -75° C. and 50 ml of water were added. The mixture was allowed to warm and the layers were separated. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from methanol/water affording the desired title product in 80% yield, m.p. 232°-234° C.

Workup

  1. temperatureto warm over 2 hours
  2. temperatureheated
  3. temperatureat reflux for 2 hours
  4. temperatureto warm
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was crystallized from methanol/water affording the desired title product in 80% yield, m.p. 232°-234° C.

Sources & evidence

ORD record
ord-891e8ef15f974cf5a1effb4c22912c19
Source dataset
uspto-grants-1990_07
Patent number
US04939163

Reaction notes

Loading…