Thionyl Chloride → 4-Bromo-2-(chloromethyl)pyridine

HRID 1446076

반응식

HRID 1446076 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[CH:3]=1.O=S(Cl)[Cl:12].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][Cl:12])[CH:3]=1

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 14761462(4-Bromopyridin-2-yl)methanol

생성물 1

HCID 533020224-Bromo-2-(chloromethyl)pyridine수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 4-bromo-2-pyridylmethanol (3.38 g, 0.016 mol) in CH2Cl2 (210 mL) was slowly added SOCl2 (21 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 20 h, then satd. NaHCO3 was added. The organic layer was washed with brine, dried (MgSO4), and concentrated to give crude 4-bromo-2-(chloromethyl)pyridine (2.93 g, 79%) as a yellow oil. APCI MS m/z 205.7, 207.7 (M+H). 1H NMR (400 MHz, (CD3)2SO) δ 8.47 (d, J=5.3 Hz, 1H), 7.68 (d, J=1.7 Hz, 1H), 7.42 (dd, J=5.3, 1.75 Hz, 1H), 4.64 (s, 2H).

후처리

  1. customat 0° C
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-807c2fcf1329462484fec43fb31911f1
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666864B2

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