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

HRID 84087Notes

Reaction equation

HRID 84087 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]([I: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]([I:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 22292815N-Trifluoroacetyl-7-hydroxy-8-iodo-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (80 mg, 0.19 mmol) in dichloromethane (3 mL) was treated with BBr3 (0.40 mL of a 1.0M solution in CH2Cl2, 0.40 mmol) and stirred overnight at 20 C. The excess BBr3 was quenched with water and the product mixture was 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 74 mg of a white solid. MS calculated for C13H13F3INO2+H: 400, observed: 400.

Workup

  1. customThe excess BBr3 was quenched with water
  2. additionthe product mixture was 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-293608cc65474b69b03c944f7e794662
Source dataset
uspto-grants-2014_09
Patent number
US08846906B2

Reaction notes

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