Boron tribromide → ({4-[3-(4-Fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)acetic Acid

HRID 392896Notes

Reaction equation

HRID 392896 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][CH3:31])[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[O:30][CH3:31])[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 tribromideHCID 10114752Ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)-acetate

Product 1

HCID 10223962({4-[3-(4-Fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl}amino)(oxo)acetic Acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

290 mg (0.64 mmol) of ethyl ({4-[3-(4-fluorobenzyl)-4-methoxybenzyl]-3,5-dimethylphenyl-}amino)(oxo)acetate (Example 3) in 8 ml of dichloromethane at −78° C. under argon are treated slowly with 356 mg (1.41 mmol) of BBr3. The mixture is allowed to fall to room temperature and is stirred for 2.5 h. The reaction mixture is poured into buffer of pH 7, the organic phase is separated off, and the pH of the aqueous phase is adjusted to pH 7 and it is then extracted. The combined organic phases are washed with saturated NaCl solution, dried and concentrated in a rotary evaporator. The residue is stirred with diethyl ether, filtered off with suction and dried.

Workup

  1. customto fall to room temperature
  2. additionThe reaction mixture is poured into buffer of pH 7
  3. customthe organic phase is separated off
  4. extractionis then extracted
  5. washThe combined organic phases are washed with saturated NaCl solution
  6. customdried
  7. concentrationconcentrated in a rotary evaporator
  8. stirringThe residue is stirred with diethyl ether
  9. filtrationfiltered off with suction
  10. customdried

Sources & evidence

ORD record
ord-d5427e479ca841fa9591fc16bb3790a3
Source dataset
uspto-grants-2004_10
Patent number
US06803480B2

Reaction notes

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