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

HRID 357719노트

반응식

HRID 357719 반응식
C1C2C(=CC=CC=2)C=C1.CCC(C[O:16][C:17](C(N(CC[NH+](C)C)C)=O)([C:24]1[CH:29]=CC=CC=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)CC.[Cl-].[Br:40]Br>O>[Br:40][C@@H:24]1[CH2:29][C:19]2[C:18](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:17]1[OH:16]

참가 물질

5

반응물 3

HCID 7219IndeneHCID 19153X 100HCID 24408Bromine

생성물 1

HCID 820607(1R,2R)-2-bromo-2,3-dihydro-1H-inden-1-ol

시약·촉매·용매 1

HCID 962Water용매

실험 절차

43.5 g of indene (92 wt %; 0.345 mol), 0.7 g of Triton X-100 and 100 ml of water were put into a 500-ml 3-mouthed flask, and mixed by stirring. Mixing was continued at 60° C. as 27.5 g of bromine (0.172 mol, 0.5 mol/mol of indene) was added dropwise over approximately 3 hours. After this, stirring at 60° C. was continued. The reaction mixture was extracted with ethyl acetate directly after dropwise addition of bromine, and after mixing for a further 1 hour. Yields of trans-2-bromoindan-1-ol were calculated from the hydrogen bromide concentrations in the aqueous phase (by gravimetric titration using silver nitrate), and the quantity of indene in the extraction layer was found by GC by means of a calibration line and used to calculate percent conversion.

후처리

  1. additionmixed
  2. additionMixing
  3. additionwas added dropwise over approximately 3 hours
  4. stirringAfter this, stirring at 60° C.
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. additiondirectly after dropwise addition of bromine
  7. additionafter mixing for a further 1 hour

출처 및 근거

ORD 기록
ord-5e3b608a02844ee681a9b9028f921b75
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05841000

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