Methanol → (5-Bromo-4-chloropyridin-2-yl)methanol

HRID 1655222ノート

反応式

HRID 1655222 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:10])[N+:5]([O-])=[CH:6][C:7]=1[Br:8].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:14].CO.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[C:7]([Br:8])=[CH:6][N:5]=[C:4]([CH2:10][OH:14])[CH:3]=1

参加物

7

反応物 4

HCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 136827785-Bromo-4-chloro-2-methylpyridine 1-oxide

生成物 1

HCID 19791171(5-Bromo-4-chloropyridin-2-yl)methanol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-chloro-5-bromo-2-picoline-N-oxide (23.9 g) in dichloromethane (250 ml) was cooled to 10° and trifluoroacetic anhydride (25 ml) added over 20 minutes. The mixture was allowed to warm to ambient temperature, and stand for 7 days. After cooling to 10°, methanol (100 ml) was added, and the solution stripped. The residue was treated with water (150 ml), basified with saturated aqueous sodium carbonate to pH 10, and extracted with ethyl acetate (2×150 ml). The combined extracts were dried (MgSO4). stripped, and triturated with ether to give 4-chloro-5-bromo-2-hydroxymethylpyridine, 16.58 g. m.p. 109°-10°.

後処理

  1. temperatureAfter cooling to 10°
  2. extractionextracted with ethyl acetate (2×150 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customtriturated with ether

出典と根拠

ORDレコード
ord-e163051bcfda47bca66e9cf94ce700db
出典データセット
uspto-grants-1993_10
特許番号
US05250527

反応ノート

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