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

HRID 474243노트

반응식

HRID 474243 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b541ef29b4274267b2d25d414c5ddd61
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637523B2

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