Carbon tetrabromide → Tert-butyl (5-bromopentan-2-yl)carbamate

HRID 474243ノート

反応式

HRID 474243 の反応式
O[CH2:2][CH2:3][CH2:4][CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>ClCCl>[Br:35][CH2:2][CH2:3][CH2:4][CH:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 545709tert-butyl N-(5-hydroxypentan-2-yl)carbamate

生成物 1

HCID 86668104Tert-butyl (5-bromopentan-2-yl)carbamate収率 53%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice-cold solution of tert-butyl (5-hydroxypentan-2-yl)carbamate (3.6 g, 17.71 mmol) in dichloromethane (150 mL) was added triphenylphosphine (6.97 g, 26.6 mmol) followed by carbon tetrabromide (8.81 g, 26.6 mmol). The reaction mixture was stirred at room temperature for 18 h while monitoring by TLC. The solvent was removed under reduced pressure and the residue was purified by column chromatography (60-120 mesh silica) using 2-5% ethyl acetate in pet-ether to give tert-butyl (5-bromopentan-2-yl)carbamate (2.5 g, 53%) as a light brown liquid. 1H NMR: (400 MHz, CDCl3) δ ppm 4.29 (1H, br s), 3.68 (1H, br s), 3.42 (2H, t, J=6.8 Hz), 1.94-1.86 (2H, m), 1.59-1.46 (2H, m), 1.44 (9H, s), 1.13 (3H, d, J=6.4 Hz).

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (60-120 mesh silica)

出典と根拠

ORDレコード
ord-b541ef29b4274267b2d25d414c5ddd61
出典データセット
uspto-grants-2014_01
特許番号
US08637523B2

反応ノート

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