N-bromobutanimide → 2-Bromo-5-chlorobenzyl bromide

HRID 1911705노트

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HRID 1911705 반응식
C(OC(N([CH2:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[Br:24])C(OC(C)(C)C)=O)=O)(C)(C)C.[Br:25]C1C=CC(Cl)=CC=1C.C1C(=O)N(Br)C(=O)C1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:24][C:18]1[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:17]=1[CH2:16][Br:25]

참가 물질

6

반응물 3

HCID 67184N-bromobutanimideHCID 844762-Bromo-5-chlorotolueneHCID 66938587N,N-bis(tert-butoxycarbonyl)-2-bromo-5-chlorobenzylamine

생성물 1

HCID 118465052-Bromo-5-chlorobenzyl bromide

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매HCID 5943Carbon Tetrachloride용매

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온도
80 °C

실험 절차

N,N-bis(tert-butoxycarbonyl)-2-bromo-5-chlorobenzylamine: To 1-bromo-4-chloro-2-methylbenzene (3.3 g, 16.06 mmol) in CCl4 (30 mL) were added NBS (3.43 g, 19.27 mmol) and benzoyl peroxide (10 mg, 0.041 mmol). The reaction was heated 80° C. overnight, then filtered and purified by flash chromatography to give 1-bromo-2-bromomethyl-4-chloro-benzene (4.5 g). 1HNMR (400 MHz, CDCl3) δ: 4.53 (s, 2H) 7.15 (dd, J=8.59, 2.27 Hz, 1H), 7.40-7.47 (m, 1H), 7.49 (d, J=8.59 Hz, 1H). This intermediate was combined with di-tert-butyl iminodicarbonate (3.49 g, 16.06 mmol) and cesium carbonate (5.23 g, 16.06 mmol) in DMF (16 mL) and stirred overnight. The reaction was partitioned with EtOAc/water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and evaporated. The resulting residue was purified by flash chromatography to give 126A (3.4 g). 1HNMR (400 MHz, CDCl3) δ: 1.43-1.51 (m, 18H), 4.82 (s, 2H), 7.08-7.18 (m, 1H), 7.39-7.53 (m, 2H).

후처리

  1. filtrationfiltered
  2. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-6830f75be4804866ae81729c668eb720
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604056B2

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