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

HRID 1757913노트

반응식

HRID 1757913 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 21218Trioctylmethylammonium chloride촉매HCID 962Water용매

실험 절차

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.

후처리

  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.)

출처 및 근거

ORD 기록
ord-ced153dbc4d64d7ca195774e8f98c735
출처 데이터셋
uspto-grants-1983_02
특허 번호
US04371389

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