Water → (S)-1,2-Difluoro-3-(1-nitrohex-5-en-2-yl)benzene

HRID 403337

반응식

HRID 403337 반응식
[N+:1](/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH:8]=[CH2:9])([O-:3])=[O:2].[F:10][C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.O.C(=O)(O)[O-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C/C(/O)=C/C(C)=O.C=C.C=C.[Rh]>[F:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([C@H:5]([CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:4][N+:1]([O-:3])=[O:2])[C:11]=1[F:10]

참가 물질

8

반응물 5

HCID 962WaterHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 2734333(2,3-Difluorophenyl)boronic acidHCID 13775677(E)-1-nitrohexa-1,5-diene

생성물 1

HCID 86681331(S)-1,2-Difluoro-3-(1-nitrohex-5-en-2-yl)benzene

시약·촉매·용매 2

HCID 11010647ethene;(Z)-4-hydroxypent-3-en-2-one;rhodium촉매HCID 312751,4-Dioxane용매

실험 절차

In a 1 L round-bottom flask was dissolved (E)-1-nitrohexa-1,5-diene (12.30 g, 97 mmol) and 2,3-difluorophenylboronic acid (38.2 g, 242 mmol) in dioxane (315 mL) to give a colorless suspension. Water (6.1 mL, 340 mmol) was added. The mixture was degassed with nitrogen and in a sonicator for 20 min. Sodium bicarbonate (4.06 g, 48.4 mmol) and (S)-(+2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.807 g, 2.90 mmol) and acetylacetonatobis(ethylene)rhodium (I) (0.749 g, 2.90 mmol) were added to the solution under nitrogen. The mixture was stirred at rt for 2 min, and then heated to 35° C. for 6 h under nitrogen. Reaction was continued for another 8 h at 35° C.

후처리

  1. customto give a colorless suspension
  2. customThe mixture was degassed with nitrogen and in a sonicator for 20 min
  3. temperatureheated to 35° C. for 6 h under nitrogen
  4. customReaction
  5. waitwas continued for another 8 h at 35° C.

출처 및 근거

ORD 기록
ord-302807f1e3ad4018bb0a6c0c084dad0a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748429B2

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