Cesium carbonate → 4-Bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene

HRID 402807

反応式

HRID 402807 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([Cl:9])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].P(OC1C=CC=CC=1)(OC1C=CC=CC=1)(O[CH2:19][CH2:20][C:21]([CH3:23])=[CH2:22])=O>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:19][CH2:20][C:21]([CH3:23])=[CH2:22])=[C:4]([Cl:9])[CH:3]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 122809773-Methylbut-3-en-1-yl diphenyl phosphateHCID 199152914-Bromo-2-chlorobenzene-1-thiol

生成物 1

HCID 667646444-Bromo-2-chloro-1-[(3-methylbut-3-en-1-yl)sulfanyl]benzene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a mixture of 4-bromo-2-chlorobenzenethiol (1.68 g, 7.54 mmol) and Cs2CO3 (4.09 g, 12.6 mmol) in DMF (8.98 mL) at room temperature was added 3-methylbut-3-en-1-yl diphenyl phosphate (2.00 g, 6.28 mmol, synthesized according to a procedure in U.S. Pat. No. 5,006,550, 9 Apr. 1991) dropwise via a syringe. The reaction mixture was heated to 85° C. for 1 hour. It was then allowed to cool to room temperature and diluted with water (20.0 mL). The resulting mixture was extracted with EtOAc:hexanes mixture (1:1, 75.0 mL, 2×) and the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The crude mixture was purified by silica gel chromatography eluting with 0-10% EtOAc/hexanes to give the desired product as a colorless oil.

後処理

  1. customsynthesized
  2. temperatureto cool to room temperature
  3. extractionThe resulting mixture was extracted with EtOAc
  4. dry with materialhexanes mixture (1:1, 75.0 mL, 2×) and the combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude mixture was purified by silica gel chromatography
  8. washeluting with 0-10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-52d20454894e4b9c9c46e84ecc2b5e20
出典データセット
uspto-grants-2014_06
特許番号
US08742110B2

関連ノート

読み込み中…