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

HRID 221241노트

반응식

HRID 221241 반응식
[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]([Br: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]([Br:19])[C:15]([OH:17])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=[O:4]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 22292777HCID 22292777, 화합물

생성물 1

HCID 22292819N-Trifluoroacetyl-8-bromo-7-hydroxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine수율 86.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of N-trifluoroacetyl-8-bromo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.50 g, 4.10 mmol) in dichloromethane (80 mL) was treated dropwise with BBr3 (9.4 mL of a 1.0M solution in CH2Cl2, 9.4 mmol), and the mixture stirred overnight while warming to 20 C. The excess BBr3 was quenched with the dropwise addition of water, the mixture 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 1.25 g of a white solid foam. 1H NMR (400 MHz, CDCl3, mixture of rotamers) d 7.25 (s, 1 H), 6.79 (m, 1 H), 3.79 (m, 1 H), 3.7-3.3 (m, 2 H), 3.2-2.8 (m, 4 H), 1.32 (m, 3 H).

후처리

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

출처 및 근거

ORD 기록
ord-8be9081a5f104cf58d288b3445cd31e8
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207158B2

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