3-Bromo-4-fluorobenzyl Alcohol → HCID 67207802, 화합물

HRID 1476065노트

반응식

HRID 1476065 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH2:5]O.[CH2:11]([O:13][C:14]([CH:16]=[PH3])=[O:15])[CH3:12]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:16][C:14]([O:13][CH2:11][CH3:12])=[O:15])[CH:7]=[CH:8][C:9]=1[F:10]

참가 물질

5

반응물 2

HCID 27733513-Bromo-4-fluorobenzyl AlcoholHCID 178473136HCID 178473136, 화합물

생성물 1

HCID 67207802HCID 67207802, 화합물

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매2회HCID 1140Toluene용매

실험 절차

9.65 g (111 mmol) of manganese dioxide were added to a solution of 6.5 g (31.7 mmol) of 3-bromo-4-fluorobenzyl alcohol and 13.25 g (38 mmol) of ethoxycarbonylmethylenephosphorane in 390 ml of toluene. The reaction mixture was heated at reflux, a further 9.65 g of manganese dioxide were added after 1 h and heating under reflux was continued overnight. After cooling, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by flash chromatography on silica gel (mobile phase cylclohexane/ethyl acetate 5:1). This gave 7.05 g (81% of theory) of the target product in the form of an E/Z isomer mixture.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered through celite
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash chromatography on silica gel (mobile phase cylclohexane/ethyl acetate 5:1)

출처 및 근거

ORD 기록
ord-462838c40a2c4dd6a4a34103807a564b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018414B2

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