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

HRID 1911705ノート

反応式

HRID 1911705 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 118465052-Bromo-5-chlorobenzyl bromide

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  1. filtrationfiltered
  2. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-6830f75be4804866ae81729c668eb720
出典データセット
uspto-grants-2013_12
特許番号
US08604056B2

反応ノート

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