Phosphorus tribromide → tert-Butyl 3-(1-bromoethyl)phenylcarbamate

HRID 2175259노트

반응식

HRID 2175259 반응식
O[CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3].[Br:18]P(Br)Br>C(Cl)Cl.C1COCC1>[Br:18][CH:2]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:8][CH:9]=1)[CH3:3]

참가 물질

5

반응물 2

HCID 24614Phosphorus tribromideHCID 16740724tert-butyl N-[3-(1-hydroxyethyl)phenyl]carbamate

생성물 1

HCID 86712586tert-Butyl 3-(1-bromoethyl)phenylcarbamate수율 78%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
5 °C

실험 절차

To a solution of tert-butyl 3-(1-hydroxyethyl)phenylcarbamate (5.8 g, 24.44 mmol) in CH2Cl2 (30 mL) and THF (20 mL) at 0° C. was added tribromophosphine (1 M solution in CH2Cl2, 24.44 mL, 24.44 mmol). The reaction was stirred at 0-10° C. for 1.5 h and then quenched with water. The mixture was extracted with CH2Cl2. The organic layer was washed with saturated NaHCO3 and brine, dried over anhydrous MgSO4, filtered and concentrated to afford the title compound (5.7 g, 78% yield) as a colorless oil. LCMS, [M+Na]+=322.1.

후처리

  1. customquenched with water
  2. extractionThe mixture was extracted with CH2Cl2
  3. washThe organic layer was washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-64a6a54f2b4940b1847a406c162fb8b2
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062028B2

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