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

HRID 36298

반응식

HRID 36298 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23964Tungsten촉매HCID 5943Carbon Tetrachloride용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-44e3ba39eab54a15a4de1eaa21287227
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

연결된 노트

불러오는 중…