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Carbon tetrabromide → 2-(6-(Bromomethyl)pyridin-2-yl)propan-2-ol

HRID 2096676
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반응식

HRID 2096676 반응식
O[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:14][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1
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참가 물질

6

반응물 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 191043162-(6-(Hydroxymethyl)pyridin-2-yl)propan-2-ol

생성물 1

HCID 667183882-(6-(Bromomethyl)pyridin-2-yl)propan-2-ol수율 74.2%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

To a solution of 2-hydroxymethyl-6-(1-hydroxy-1-methylethyl)pyridine (5.1 g, 30.5 mmol) in dichloromethane (300 mL) was added carbon tetrabromide (8.81 g, 33.6 mmol) and triphenylphosphine (11.14 g, 33.6 mmol). The reaction was stirred at ambient temperature overnight then poured into a saturated solution of sodium bicarbonate. The organic layer was separated, concentrated to dryness and purified by column chromatography, eluting with a gradient of hexane to 3:1 hexane:ethyl acetate. The title compound (5.21 g, 74%) was obtained as a colourless oil; LC-MS Retention time 2.08 min, (M+H)+ 230, 232

후처리

  1. customThe organic layer was separated
  2. concentrationconcentrated to dryness
  3. custompurified by column chromatography
  4. washeluting with a gradient of hexane to 3:1 hexane

출처 및 근거

ORD 기록
ord-9eb25747eb564f8482917e17d353fb85
출처 데이터셋
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08450328B2

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