Potassium Carbonate → 1-Bromo-3-propylsulfanylbenzene

HRID 20425

反応式

HRID 20425 の反応式
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH3:10].[Br:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1>CC(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH2:8][CH2:9][CH3:10])[CH:13]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 80597m-Bromobenzenethiol

生成物 1

HCID 544502371-Bromo-3-propylsulfanylbenzene収率 95%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Reflux a suspension of potassium carbonate (22.4 g), 1-iodopropane (10.3 mL) and 3-bromothiophenol (8.4 mL) in acetone (375 mL) for 5 hours. Cool to room temperature, filter through diatomaceous earth, and concentrate. Dissolve the residue in hexanes, filter through a silica gel plug, and concentrate to give 1-bromo-3-propylsulfanylbenzene (18 g, 95%) as an oil (GC-MS: m/z=231). Add this material (12 g) to a solution of n-butyllithium (57 mmol) in THF (50 mL) at −78° C. Stir for 45 min, add 110 N,N-dimethylformamide (8.1 mL) and warm to room temperature. Stir for 15 min, pour into water (175 mL), and extract into diethyl ether (3×200 mL). Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography) to give the title compound (7.3 g, 92%).

後処理

  1. temperatureReflux
  2. filtrationfilter through diatomaceous earth
  3. concentrationconcentrate
  4. dissolutionDissolve the residue in hexanes
  5. filtrationfilter through a silica gel plug
  6. concentrationconcentrate

出典と根拠

ORDレコード
ord-422691bbe5ff4985b7488402fa4ddc6f
出典データセット
uspto-grants-2010_06
特許番号
US07745438B2

関連ノート

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