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

HRID 703137Notes

Reaction equation

HRID 703137 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-993a79a73ff4495abfb12b76c418d617
Source dataset
uspto-grants-1991_01
Patent number
US04981866

Reaction notes

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