Boron tribromide → HCID 20775662, compound

HRID 1815991Notes

Reaction equation

HRID 1815991 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20775664HCID 20775664, compound

Product 1

HCID 20775662HCID 20775662, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl (±)-4-(4-methoxyphenyl)-3-[4-(trifluoromethyl)phenyl]butanoate (450 mg, 1.23 mmole) in CH2Cl2 (5 mL) was added BBr3 (1.5 mL, 1.48 mmole) at −10° C. After 3 hr the mixture was carefully quenched with EtOH (10 mL), and the solution was allowed to warm to RT. The mixture was concentrated, and the residue was chromatographed on silica gel (20% EtOAc/hexanes) to give the title compound (270 mg, 63%) as a yellow oil: TLC (20% EtOAc/hexanes) Rf0.22.

Workup

  1. customAfter 3 hr the mixture was carefully quenched with EtOH (10 mL)
  2. concentrationThe mixture was concentrated
  3. customthe residue was chromatographed on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7019983b1d78498db61975fff7768ea7
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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