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

HRID 1035379Notes

Reaction equation

HRID 1035379 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4].B(Br)(Br)Br>ClCCl>[F:20][C:2]([F:1])([F:19])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22292800HCID 22292800, compound

Product 1

HCID 22292790N-Trifluoroacetyl-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3benzazepineYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-trifluoroacetyl-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.506 g, 1.76 mmol) in dichloromethane (20 mL) was treated with BBr3 (4.1 mL of a 1.0M solution in CH2Cl2, 4.1 mmol) and stirred overnight while warming to 20 C. The excess BBr3 was quenched with water, and the resulting mixture was diluted with ether (200 mL), washed with Na2CO3 (100 mL) and brine (100 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.460 g of a white solid foam. MS calculated for C13H14F3NO2+H: 274, observed: 274.

Workup

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 was quenched with water
  3. additionthe resulting mixture was diluted with ether (200 mL)
  4. washwashed with Na2CO3 (100 mL) and brine (100 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c7edd637652e4febae34e5ea62eb8562
Source dataset
uspto-grants-2013_10
Patent number
US08546379B2

Reaction notes

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