Carbon tetrabromide → 2-Bromomethyl-6-(1-methoxy-1-methylethyl)pyridine

HRID 2096703노트

반응식

HRID 2096703 반응식
[C:1]([Br:5])(Br)(Br)Br.OC[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:17][CH3:18])([CH3:16])[CH3:15])[N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:5][CH2:1][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([O:17][CH3:18])([CH3:15])[CH3:16])[N:9]=1

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 667184342-Hydroxymethyl-6-(1-methoxy-1-methylethyl)pyridine

생성물 1

HCID 667183972-Bromomethyl-6-(1-methoxy-1-methylethyl)pyridine수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Carbon tetrabromide (1.59 g, 4.80 mmol) was added portionwise to a stirred solution of 2-hydroxymethyl-6-(1-methoxy-1-methylethyl)pyridine (724 trig, 4.00 mmol) and triphenylphosphine (1.15 g, 4.40 mmol) in DCM (50 mL) at 0° C. The mixture was stirred at 0° C. for 1 h then concentrated in vacuo. The residue was purified by column chromatography (20:1 to 5:1 isohexane:EtOAc) to give the title compound (732 mg, 75%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.69-7.65 (1H, m), 7.46-7.43 (1H, m), 7.32-7.30 (1H, m), 4.55 (2H, s), 3.17 (3H, s), 1.55 (6H, s).

후처리

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by column chromatography (20:1 to 5:1 isohexane:EtOAc)

출처 및 근거

ORD 기록
ord-3df940defefc4c4781c5a091d836fa82
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450328B2

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