Hexamethylphosphoramide → 7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one

HRID 2096606노트

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HRID 2096606 반응식
[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH:8]=[CH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.CN(P(N(C)C)(N(C)C)=O)C.[C:25]1([Mg]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][CH2:7][CH:8]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

참가 물질

5

반응물 3

HCID 12679HexamethylphosphoramideHCID 542267847-bromobenzo[b]oxepin-5(2H)-oneHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 584241057-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one수율 17%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 7-bromobenzo[b]oxepin-5(2H)-one (1.33 g, 5.6 mmol), CuBr—SMe2(60 mg, 0.3 mmol) and HMPA (2.058 g, 11.5 mmol) in THF (30 mL) was added phenylmagnesium bromide (3.0 M, 3.7 mL) at −78° C., the mixture was stirred at −78° C. for 1 hour. The mixture was quenched by HCl (10%, 5 mL), extracted with ethoxyethane, and then washed with NaHCO3, brine, dried over Na2SO4, concentrated and purified by column chromatography to give 7-bromo-3-phenyl-3,4-dihydrobenzo[b]oxepin-5(2H)-one (300 mg, 17%). 1H-NMR(CH2D2): 3.11 (m, 2H), 3.49 (m, 1H), 4.28 (m, 2H), 6.93 (m, 1H), 7.17 (m, 1H), 7.23 (m, 4H), 7.45 (m, 1H), 7.83 (m, 1H)

후처리

  1. customThe mixture was quenched by HCl (10%, 5 mL)
  2. extractionextracted with ethoxyethane
  3. washwashed with NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-7471d846756446ca8724664c8e774c83
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450308B2

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