Diethyl Ether → Methyl 2-bromomethyl-5-[4-(trifluoromethyl)phenyl]-3-furoate

HRID 9643

反応式

HRID 9643 の反応式
[Br:1]([O-])(=O)=O.[Na+].[CH3:6][C:7]1[O:8][C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13].S([O-])(O)=O.[Na+].C(OCC)C>O.C1CCCCC1>[Br:1][CH2:6][C:7]1[O:8][C:9]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:25])[F:24])=[CH:18][CH:17]=2)=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 21986466Methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate2 回HCID 23665763Sodium BisulfiteHCID 23668195Sodium Bromate

生成物 1

HCID 21986318Methyl 2-bromomethyl-5-[4-(trifluoromethyl)phenyl]-3-furoate

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8078Cyclohexane溶媒

反応条件

温度
10 °C

実験手順

A solution of sodium bromate (8.14 g) in water (27 ml) was treated with a suspension of methyl 2-methyl-5-[4-(trifluoromethyl)phenyl]-3-furoate (intermediate 23, 5.12 g) in cyclohexane (36 ml). The system was cooled to <10° C. in ice/water bath and treated with a solution of sodium hydrogen sulfite (9.4 g) in water (54 ml) in a drop-wise manner over 30 minutes. The reaction was allowed to warm up to 10° C. for 2 hours and then poured into diethylether (400 ml) and washed with fresh water. The organic layer was washed with 10% sodium thiosulfite solution and dried over magnesium sulfate. The crude product isolated by evaporation, was pre-adsorbed onto silica and purified by flash column chromatography using 39:1 cyclohexane:ethyl acetate as eluent to give the title compound as a white powder.

後処理

  1. washwashed with fresh water
  2. washThe organic layer was washed with 10% sodium thiosulfite solution
  3. dry with materialdried over magnesium sulfate
  4. customThe crude product isolated by evaporation
  5. custompurified by flash column chromatography

出典と根拠

ORDレコード
ord-2e4f1814c45a4d49ad767afa4112ca37
出典データセット
uspto-grants-2006_08
特許番号
US07091237B2

関連ノート

読み込み中…