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

HRID 1376245

反応式

HRID 1376245 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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]−).

後処理

  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

出典と根拠

ORDレコード
ord-fcc48195aafe4bc58d90fe2f92ee75b7
出典データセット
uspto-grants-2007_01
特許番号
US07169942B2

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