Boron tribromide → HCID 22292839, compound

HRID 881956Notes

Reaction equation

HRID 881956 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([O:17]C)=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:20])=[O:4].B(Br)(Br)Br>ClCCl>[F:21][C:2]([F:1])([F:22])[C:3]([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([Br:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH:6]1[CH3:20])=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22292813N-Trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro 1H-3-benzazepine

Product 1

HCID 22292839HCID 22292839, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of N-trifluoroacetyl-8-bromo-1,4-dimethyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (0.383 g, 1.01 mmol) in dichloromethane (30 mL) was treated with BBr3 (2.35 mL of a 1.0M solution in CH2Cl2, 2.35 mmol) and stirred overnight while warming to 20 C. The excess BBr3 is quenched with water, and the resulting mixture was diluted with ether (100 mL), washed with saturated aqueous Na2CO3 (50 mL) and brine (50 mL), dried with Na2SO4 and concentrated. Flash chromatography (15% EtOAc in hexane, silica) resulted in 0.302 g of a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.22 (m, 1H), 6.77 (m, 1H), 5.34 (s, 1H), 4.35 (m, 1H), 3.62 (m, 1H), 3.24 (m, 1H), 3.13 (m, 2H), 2.69 (m, 1H), 1.31 (m, 3H), 1.22 (m, 3H).

Workup

  1. temperaturewhile warming to 20 C
  2. customThe excess BBr3 is quenched with water
  3. additionthe resulting mixture was diluted with ether (100 mL)
  4. washwashed with saturated aqueous Na2CO3 (50 mL) and brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9145adcaa5c44f56888c6a1a58252d84
Source dataset
uspto-grants-2015_03
Patent number
US08993750B2

Reaction notes

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