Hydrogen Bromide → 3-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine

HRID 271457노트

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HRID 271457 반응식
[CH3:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[C:4]([C:10]([F:13])([F:12])[F:11])[N:3]=1.[BrH:14]>>[Br:14][CH2:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:10]([F:13])([F:12])[F:11])=[CH:5][CH:6]=1

참가 물질

3

반응물 2

HCID 260Hydrogen BromideHCID 2760122(2-Methyl-6-(trifluoromethyl)pyridin-3-yl)methanol

생성물 1

HCID 598348213-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine수율 71%

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온도
135 °C

실험 절차

A mixture of (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (1.677 g, 8.77 mmol, 76% pure) in 48% aq. HBr (10 mL) was heated to reflux (oil bath temperature, 135° C.) for 24 h. The volatile components of the resulting biphasic mixture were distilled under vacuum to remove most of the hydrogen bromide (sodium hydroxide trap). The residue was partitioned between 2:1 EtOAc/THF and water (at pH 3) and the organic phase was dried (MgSO4), filtered and evaporated. The solid residue was re-evaporated after addition of dichloromethane/hexanes to obtain the title compound as a tan solid, 1.19 g, 71% yield (based on the purity of the starting material). HPLC/MS: retention time=2.15 min, [M+H]30 =254.

후처리

  1. temperaturewas heated
  2. distillationThe volatile components of the resulting biphasic mixture were distilled under vacuum
  3. customto remove most of the hydrogen bromide (sodium hydroxide trap)
  4. customThe residue was partitioned between 2:1 EtOAc/THF and water (at pH 3)
  5. dry with materialthe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was re-evaporated
  9. additionafter addition of dichloromethane/hexanes

출처 및 근거

ORD 기록
ord-e6e5ef9fbfeb452595567ab337decb6b
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452892B2

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