Benzyl Bromide → 2-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole

HRID 355027ノート

反応式

HRID 355027 の反応式
[Cl:1][C:2]1[S:3][C:4]([CH2:11][OH:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCCCCC.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[Cl:1][C:2]1[S:3][C:4]([CH2:11][O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:5]([C:7]([F:8])([F:9])[F:10])[N:6]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 14798Sodium HydroxideHCID 12953359(2-Chloro-4-(trifluoromethyl)thiazol-5-yl)methanol

生成物 1

HCID 129533662-Chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole収率 81.2%

試薬・触媒・溶媒 2

HCID 21218Trioctylmethylammonium chloride触媒HCID 962Water溶媒

実験手順

A mixture of 4.34 g (0.02 mol) of the compound of Example 4, 14.1 g (0.0825 mol) of benzyl bromide, 0.1 g of Aliquat 336 (tradename of phase transfer catalyst available from the General Mills Co.) 25 ml of hexane, 15 ml of 50% sodium hydroxide, and 15 ml of water was held at reflux for 30 minutes. The hexane layer was separated, dried over MgSO4 and concentrated under reduced pressure. The residue (6.8 g) was Kugelrohr distilled at 2 mm (pot temperature 120°-130° C.) to give 5.0 g (81% yield) of 2-chloro-4-(trifluoromethyl)-5-[(benzyloxy)-methyl]-thiazole nD25 1.5215.

後処理

  1. temperatureat reflux for 30 minutes
  2. customThe hexane layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled at 2 mm (pot temperature 120°-130° C.)

出典と根拠

ORDレコード
ord-cf71c2a25c6c4ed9bdffff403d63cce2
出典データセット
uspto-grants-1983_03
特許番号
US04377693

反応ノート

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