Boron tribromide → ({4-[3-(4-Fluorobenzyl)-4-hydroxy-benzyl]-3,5-dimethylphenyl}amino)(oxo)acetic acid

HRID 392895Notes

Reaction equation

HRID 392895 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[O:30]C)[CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([NH:18][C:19](=[O:25])[C:20]([O:22]CC)=[O:21])=[CH:13][C:12]=2[CH3:26])=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([CH:27]=[CH:28][C:29]=2[OH:30])[CH2:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14]([NH:18][C:19](=[O:25])[C:20]([OH:22])=[O:21])=[CH:13][C:12]=2[CH3:26])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 10114752Ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)-acetate

Product 1

HCID 10294819({4-[3-(4-Fluorobenzyl)-4-hydroxy-benzyl]-3,5-dimethylphenyl}amino)(oxo)acetic acidYield 56.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

102 mg (0.22 mmol) of ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)acetate (Example 3) in 5 ml of dichloromethane at −78° C. under argon are treated slowly with 65 mg (0.25 mmol) of BBr3. The reaction mixture is stirred overnight while reaching room temperature. It is again cooled to −78° C. and a further 65 mg (0.25 mmol) of BBr3 is added. The mixture is stirred at room temperature for 2 hours. Pouring into ice-water, stirring for 2 hours, extraction with dichloromethane and ethyl acetate and drying over sodium sulphate are followed by concentration in a rotary evaporator. The residue is stirred with ether and the solid is filtered off with suction. 51 mg (48%) of ({4-[3-(4-fluorobenzyl)-4-hydroxy-benzyl]-3,5-dimethylphenyl}amino)(oxo)acetic acid are obtained.

Workup

  1. customwhile reaching room temperature
  2. stirringThe mixture is stirred at room temperature for 2 hours
  3. stirringstirring for 2 hours
  4. extractionextraction with dichloromethane and ethyl acetate
  5. dry with materialdrying over sodium sulphate
  6. concentrationare followed by concentration in a rotary evaporator
  7. stirringThe residue is stirred with ether
  8. filtrationthe solid is filtered off with suction

Sources & evidence

ORD record
ord-72c82fd752494a9f9c95e14df8cc255a
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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