Boron tribromide → N-Trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 2389432Notes

Reaction equation

HRID 2389432 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([O:19]C)=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:23][C:2]([F:1])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH:12]([CH3:14])[CH3:13])[C:9]2[CH:15]=[C:16]([Br:21])[C:17]([OH:19])=[CH:18][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22292805N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292823N-Trifluoroacetyl-8-bromo-7-hydroxy-1-isopropyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 97.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-trifluoroacetyl-8-bromo-1-isopropyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.041 g, 0.10 mmol) in dichloromethane (1 mL) was treated with BBr3 (0.32 ml, 1.0 M solution in CH2Cl2) and stirred overnight at 20 C. The excess BBr3 is quenched with water and the resulting mixture diluted with ether (50 mL), washed twice with saturated aqueous Na2CO3 (20 mL) and concentrated. Flash chromatography (20% EtOAc in hexanes, silica) resulted in 0.037 g clear oil. MS calculated for C15H17BrF3NO2+H: 380, observed: 380.

Workup

  1. customThe excess BBr3 is quenched with water
  2. additionthe resulting mixture diluted with ether (50 mL)
  3. washwashed twice with saturated aqueous Na2CO3 (20 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d1a2ce24762843ee84ffde44f03d8196
Source dataset
uspto-grants-2012_09
Patent number
US08273734B1

Reaction notes

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