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

HRID 1762864Notes

Reaction equation

HRID 1762864 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 fromm 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 fromm methanol/water affording the desired title product in 80% yield, m.p. 232°-234° C.

Sources & evidence

ORD record
ord-53d21b2049e24f46b46c6f8d31d406fd
Source dataset
uspto-grants-1989_05
Patent number
US04835181

Reaction notes

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