Bromine → 4'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamide

HRID 36298

反応式

HRID 36298 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15](=[O:22])(=[O:21])[NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:23]Br>C(Cl)(Cl)(Cl)Cl.[W]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15](=[O:22])(=[O:21])[NH:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:5]=[CH:6][C:7]=1[CH2:8][Br:23]

参加物

5

反応物 2

HCID 24408BromineHCID 100874243-Fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl

生成物 1

HCID 100465214'-(Bromomethyl)-N-t-butyl-3'-fluoro-2-biphenylsulfonamide収率 81.8%

試薬・触媒・溶媒 2

HCID 23964Tungsten触媒HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

A solution of 1.08 g (3.36 mmol) of 3-fluoro-4-methyl-2'-(N-t-butylsulfamoyl)biphenyl (from Step A) in 20 mL of CCl4 was stirred at reflux under irradiation from a 100-watt tungsten lamp as a solution of 3.5 mmol of bromine in approximately 13 mL of CCl4 was added dropwise over 1.5 hour. After being stirred at reflux overnight, the solution was cooled and concentrated. The residue was crystallized from EtOAc-hexane to give 1.10 g of the title compound as an off-white solid, mp 138°-140° C. (estimated purity 87%; contained minor unbrominated and dibrominated contaminants by TLC); mass spectrum (FAB) m/e 400, 402 (M+1)+.

後処理

  1. additionwas added dropwise over 1.5 hour
  2. temperatureat reflux overnight
  3. temperaturethe solution was cooled
  4. concentrationconcentrated
  5. customThe residue was crystallized from EtOAc-hexane

出典と根拠

ORDレコード
ord-44e3ba39eab54a15a4de1eaa21287227
出典データセット
uspto-grants-1995_05
特許番号
US05411980

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