Boron tribromide → HCID 22292839, 화합물

HRID 84113노트

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HRID 84113 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 22292839HCID 22292839, 화합물수율 81.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e28941f4afee40b1a8103cadcb01eea0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846906B2

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