Boron tribromide → 5-(2-Butyl-1,3-dithiolan-2-yl)benzene-1,3-diol

HRID 1376245

반응식

HRID 1376245 반응식
B(Br)(Br)Br.[CH2:5]([C:9]1([C:14]2[CH:19]=[C:18]([O:20]C)[CH:17]=[C:16]([O:22]C)[CH:15]=2)[S:13][CH2:12][CH2:11][S:10]1)[CH2:6][CH2:7][CH3:8]>C(Cl)Cl>[CH2:5]([C:9]1([C:14]2[CH:15]=[C:16]([OH:22])[CH:17]=[C:18]([OH:20])[CH:19]=2)[S:10][CH2:11][CH2:12][S:13]1)[CH2:6][CH2:7][CH3:8]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 3176902-Butyl-2-(3,5-dimethoxy-phenyl)-[1,3]dithiolane

생성물 1

HCID 3176955-(2-Butyl-1,3-dithiolan-2-yl)benzene-1,3-diol수율 77.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Boron tribromide (32.9 ml of 1M soln, 32.9 mmol) was added to a solution of Compound 9 (4.51 g, 3.23 mmol) in CH2Cl2 (546 ml) under argon at −78° C. The reaction temperature was then raised slowly to 0° C. over a period of 3 hrs. Stirring was continued at 0° C. for 12–14 hrs or until completion of reaction. Unreacted boron tribromide was destroyed by adding methanol, solvent removed and the residual oil diluted with diethyl ether. The organic phase was washed with saturated NaHCO3, water and brine, dried and concentrated. The residue was resolved over silica gel eluting with diethylether/hexanes (4:6) to yield 0.675 g (74.1%) of Compound 16 as a waxy solid. Rf=0.28 (hexane:ethyl acetate 8:2) 1H NMR δ 6.79 (d, J=2.5 Hz, 2H), 6.23 (t, J=2H, 1H), 5.30 (br s, 2H), 3.38–3.19 (m, 4H), 2.25 (t, J=9.75 Hz, 2H), 1.29–1.18 (m, 4H), 0.83 (t, J=7 Hz, 3H); 13C NMR δ 156.24, 148.45, 107.23, 101.50, 73.90, 45.50, 39.01, 29.96, 22.74, 13.86; MS: (ESI, Neg.) m/z 269 ([M−H]−).

후처리

  1. customwas continued at 0° C. for 12–14 hrs or until completion of reaction
  2. customUnreacted boron tribromide was destroyed
  3. additionby adding methanol, solvent
  4. customremoved
  5. additionthe residual oil diluted with diethyl ether
  6. washThe organic phase was washed with saturated NaHCO3, water and brine
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fcc48195aafe4bc58d90fe2f92ee75b7
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169942B2

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