Thionyl Chloride → (E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene

HRID 1767133노트

반응식

HRID 1767133 반응식
S(Cl)([Cl:3])=O.N1C2C=CC=CC=2N=N1.[F:14][C:15]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:16]=1[CH:17]=[CH:18][CH2:19]O>ClCCl>[Cl:3][CH2:19]/[CH:18]=[CH:17]/[C:16]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:15]=1[F:14]

참가 물질

5

반응물 3

HCID 24386Thionyl ChlorideHCID 534015802,5-Difluorocinnamyl alcoholHCID 178418385HCID 178418385, 화합물

생성물 1

HCID 11608064(E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of 0.66 cm3 (9.07 mmol) of thionyl chloride and 1.08 g (9.07 mmol) of benzotriazole in 70 cm3 of dichloromethane are added at a temperature in the region of 20° C., under an argon atmosphere, to 1.25 g (7.34 mmol) of 2,5-difluorocinnamyl alcohol in solution in 130 cm3 of dichloromethane. After stirring for 10 minutes, the reaction mixture is filtered on No. 3 sintered glass and the solid residue rinsed with twice 20 cm3 of dichloromethane. The filtrate is washed with 3 times 75 cm3 of water. The organic phase is dried over anhydrous magnesium sulfate and filtered to give a solution of 2-[(1E)-3-chloro-1-propenyl]-1,4-difluorobenzene (7.34 mmol) which is immediately used as it is in the next step.

후처리

  1. filtrationthe reaction mixture is filtered on No
  2. wash3 sintered glass and the solid residue rinsed with twice 20 cm3 of dichloromethane
  3. washThe filtrate is washed with 3 times 75 cm3 of water
  4. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  5. filtrationfiltered

출처 및 근거

ORD 기록
ord-8b311139721941669c8673fb1b52d995
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232833B2

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