Dimethyl Sulfoxide → 3-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE

HRID 1919798ノート

反応式

HRID 1919798 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]([S:15][C:16]1[CH:17]=[C:18]([CH2:22][OH:23])[CH:19]=[CH:20][CH:21]=1)([F:14])[F:13].C(N(CC)CC)C>ClCCl.O>[F:11][C:12]([S:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[CH:22]=[O:23])([F:14])[F:13]

参加物

7

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 27778683-(Trifluoromethylthio)benzyl alcohol

生成物 1

HCID 27778433-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE収率 91%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-78 °C

実験手順

Add a solution of dimethyl sulfoxide (0.82 mL, 11.5 mmol) in dichloromethane (2 mL) over a period of 5 minutes to a solution of oxalyl chloride (0.46 mL, 5.28 mmol) in dichloromethane (10 mL) cooled to −78° C. Stir 10 minutes then add a solution of (3-trifluoromethylsulfanyl-phenyl)-methanol (1.00 g, 4.80 mmol) in dichloromethane (4 mL). Stir 15 minutes then add triethylamine (3.35 mL, 24.0 mmol). Slowly warm to ambient temperature, add water and separate the organic layer. Extract the aqueous layer with dichloromethane. Dry (sodium sulfate) the combined organic layers, filter, and concentrate in vacuo. Purify by silica gel chromatography (10% ethyl acetate/hexane) to afford the titled compound as a yellow liquid (896 mg, 91%). 1H NMR (400 MHz, DMSO) δ 7.74 (dd, J=7.6, 7.6, 1H), 8.01 (d, J=7.9, 1H), 8.09 (d, J=7.5, 1H), 8.12 (s, 1H), 10.03 (s, 1H).

後処理

  1. stirringStir 15 minutes
  2. temperatureSlowly warm to ambient temperature
  3. customseparate the organic layer
  4. extractionExtract the aqueous layer with dichloromethane
  5. dry with materialDry (sodium sulfate) the combined organic layers
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by silica gel chromatography (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-d793445ddf6844ae8125032ab0ae1e25
出典データセット
uspto-grants-2012_05
特許番号
US08168659B2

反応ノート

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