Benzyl Bromide → 1-benzyl-2-trifluoromethyl-(1H)-indole

HRID 231839

반응식

HRID 231839 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(O)(O)([O-])=O.[Na+]>O1CCCC1.O>[CH2:16]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:3]1[C:2]([F:1])([F:12])[F:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 109321242-(trifluoromethyl)-1H-indoleHCID 23672064Monosodium phosphate

생성물 1

HCID 178825801-benzyl-2-trifluoromethyl-(1H)-indole

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

8.6 g of 2-trifluoromethyl-(1H)-indole and 100 ml of tetrahydrofuran were mixed together under an inert atmosphere and cooled to 0° C. Over 15 minutes, about 2.4 g of a suspension of sodium hydride at 50% in oil was added in small fractions and 6.5 ml of benzyl bromide in solution in 10 ml of tetrahydrofuran were introduced over 5 minutes. The mixture was stirred for 42 hours at ambient temperature and then was poured into water saturated with monosodium phosphate. The mixture was extracted with ethyl ether, and the extracts were dried and concentrated to dryness by distillation under reduced pressure. The residue was chromatographed over silica and eluted with a mixture of hexane and ethyl acetate (9/1) to obtain 12.54 g of 1-benzyl-2-trifluoromethyl-(1H)-indole melting at approx. 20° C.

후처리

  1. additionwere introduced over 5 minutes
  2. extractionThe mixture was extracted with ethyl ether
  3. customthe extracts were dried
  4. concentrationconcentrated to dryness by distillation under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with a mixture of hexane and ethyl acetate (9/1)

출처 및 근거

ORD 기록
ord-6aba9620a94d47ac8f394f06fb33675d
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04849443

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