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

HRID 1446076

反応式

HRID 1446076 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 533020224-Bromo-2-(chloromethyl)pyridine収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-807c2fcf1329462484fec43fb31911f1
出典データセット
uspto-grants-2010_02
特許番号
US07666864B2

関連ノート

読み込み中…