Hydrogen Peroxide → (1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol

HRID 357721

반응식

HRID 357721 반응식
CCC(C[O:7][C:8](C(N(CC[NH+](C)C)C)=O)([C:15]1[CH:20]=CC=CC=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)CC.[Cl-].C1C2C(=CC=CC=2)C=C1.[Br:40]Br.OO>ClC1C=CC=CC=1Cl.O>[Br:40][C@@H:15]1[CH2:20][C:10]2[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:8]1[OH:7]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 7219IndeneHCID 19153X 100HCID 24408Bromine

생성물 1

HCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
20 °C

실험 절차

100 ml of water and 0.70 g of Triton X-100 were put into a 300-ml 4-mouthed flask, and mixed as 80 ml of ortho-dichlorobenzene and 60.0 g of indene (95 wt %; 0.491 mol) were added. At 20° C., 41.54 g of bromine (0.259 mol) was added with strong stirring and air cooling over approximately 5 minutes. After dropwise addition the temperature of the reaction mixture became 52° C. After mixing at 60° C. for 13 hours, 23.8 g of hydrogen peroxide (35 wt %; 0.245 mol) was added dropwise at the same temperature, requiring 3 hours, followed by mixing for a further 3 hours at 60° C. and then separation into an aqueous layer and a slurry layer. The aqueous layer was extracted with 120 ml of ortho-dichlorobenzene, and the extract layer was bulked with the earlier slurry layer. The warm slurry layer was cooled gradually to 20° C. under stirring, the crystals which came down were isolated by centrifugation and washed with 30 ml of ortho-dichlorobenzene. The wet crystals were dried at 65°-70° C. under decreased pressure to obtain 72.18 g of white crystals of trans-2-bromoindan-1-ol (yield 69.0%).

후처리

  1. additionwere added
  2. temperatureair cooling over approximately 5 minutes
  3. additionAfter dropwise addition the temperature of the reaction mixture
  4. custombecame 52° C
  5. additionAfter mixing at 60° C. for 13 hours
  6. additionby mixing for a further 3 hours at 60° C.
  7. customseparation into an aqueous layer
  8. extractionThe aqueous layer was extracted with 120 ml of ortho-dichlorobenzene
  9. stirringunder stirring
  10. customthe crystals which came down were isolated by centrifugation
  11. washwashed with 30 ml of ortho-dichlorobenzene
  12. customThe wet crystals were dried at 65°-70° C.

출처 및 근거

ORD 기록
ord-27dd2504458f46eb87c14b0097ac52a5
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05841000

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