Carbon tetrabromide → (Z)-3-(2-Bromoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

HRID 379625ノート

反応式

HRID 379625 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22]O.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:25][CH2:22][CH2:21][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)/[C:7](=[CH:11]\[C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)/[C:6]=1[CH3:20]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 70229088(Z)-5-Fluoro-3-(2-hydroxyethyl)-2-methyl-1-(4-methylthiobenzylidene)indene

生成物 1

HCID 70230765(Z)-3-(2-Bromoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a solution of the alcohol from Step 1 (4.8 g, 14.7 mmol) and carbon tetrabromide (6.34 g, 19.1 mmol) in methylene chloride (100 mL) at 0° C. there was added, in portions, 1,2-bis(diphenylphosphino)ethane (6.34 g, 17.3 mmol). The mixture was stirred at 0° C. for 1 hour, and the solvent was evaporated. The residue was stirred in a mixture of ethyl acetate and water (150 mL each) for 30 minutes. After filtration, the organic portion of the filtrate was evaporated and the crude product purified by column chromatography on silica gel using 10% ethyl acetate in hexane as eluent to afford pure title compound as a yellow oil which solidified on standing.

後処理

  1. customthe solvent was evaporated
  2. stirringThe residue was stirred in a mixture of ethyl acetate and water (150 mL each) for 30 minutes
  3. filtrationAfter filtration
  4. customthe organic portion of the filtrate was evaporated
  5. customthe crude product purified by column chromatography on silica gel using 10% ethyl acetate in hexane as eluent

出典と根拠

ORDレコード
ord-09d276929c8e40a4a25f597b5d88eabb
出典データセット
uspto-grants-2001_10
特許番号
US06300346B1

反応ノート

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