Boron tribromide → HCID 22292779, compound

HRID 1689686Notes

Reaction equation

HRID 1689686 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:19])[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:21])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Cl:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22292769HCID 22292769, compound

Product 1

HCID 22292779HCID 22292779, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of N-trifluoroacetyl-8-chloro-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (48 mg, 0.15 mmol) in dichloromethane (2 mL) was treated with BBr3 (0.30 mL of a 1.0M solution in CH2Cl2, 0.30 mmol) and stirred overnight at 20° C. The excess BBr3 was quenched with water and the resulting mixture diluted with ether (20 mL), washed with Na2CO3 (10 mL) and brine (10 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 24 mg of a white solid. MS calculated for C13H13ClF3NO2+H: 308, observed: 308.

Workup

  1. customThe excess BBr3 was quenched with water
  2. additionthe resulting mixture diluted with ether (20 mL)
  3. washwashed with Na2CO3 (10 mL) and brine (10 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-180d00fa03474a9eb271f1e1f9718bcc
Source dataset
uspto-grants-2012_04
Patent number
US08153621B2

Reaction notes

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