1,4-Dibromobenzene → HCID 131733144, 화합물

HRID 1525295노트

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HRID 1525295 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li][CH2:10][CH2:11][CH2:12][CH3:13].C1(/C=[N:21]/[S@:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])CCCCC1.[CH2:28]1[CH2:32]OC[CH2:29]1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:10]([CH2:25][C:24]([CH3:27])([S@@:22]([NH2:21])=[O:23])[CH3:26])[CH:11]2[CH2:32][CH2:28][CH2:29][CH2:13][CH2:12]2)=[CH:3][CH:4]=1

참가 물질

5

반응물 4

HCID 78041,4-DibromobenzeneHCID 8028Tetrahydrofuran2회HCID 16655337HCID 16655337, 화합물2회HCID 178418339Butyllithium

생성물 1

HCID 131733144HCID 131733144, 화합물수율 22.33%

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온도
-70 °C

실험 절차

1,4-dibromobenzene (20 g, 84.7 mmol) was dissolved in anhydrous THF (300 ml) and the resulting mixture was then cooled to −70° C. Then BuLi (34 mL, 84.6 mmol) was added dropwise at that temperature. The mixture was stirred at −70° C. for 1 hour, then (S,E)-N-(cyclohexylmethylene)-2-methylpropane-2-sulfinamide, 27-a, (14 g, 65 mmol) in anhydrous THF (30 ml) was added dropwise into the mixture at −70° C. The mixture was then stirred overnight from −70° C. to 10° C. The mixture was quenched with saturated NH4Cl followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1) to provide the product, 27-b, (5.4 g, 22.33%). HPLC indicated that the reaction underwent excellent stereoselectivity.

후처리

  1. stirringThe mixture was then stirred overnight from −70° C. to 10° C
  2. customThe mixture was quenched with saturated NH4Cl
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (petroleum ether/ethyl acetate=30/1)

출처 및 근거

ORD 기록
ord-40e6d54530ee4527b8485efaecf10aba
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079930B2

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