Potassium Carbonate → 3-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde

HRID 68608

反応式

HRID 68608 の反応式
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].Br[C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([S:22]([CH3:25])(=[O:24])=[O:23])[CH:16]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[CH:8]=[C:3]([CH:4]=[CH:5][C:6]=2[O:12][CH3:13])[CH:1]=[O:2])=[CH:16][C:17]=1[S:22]([CH3:25])(=[O:23])=[O:24]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 269854244-Bromo-1-fluoro-2-(methylsulphonyl)benzene

生成物 1

HCID 866818393-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde収率 108.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
140 °C

実験手順

To a solution of 5-Formyl-2-methoxyphenylboronic acid (324 mg, 1.8 mmol, 1.5 eq, Frontier Scientific, Inc., Logan, Utah, USA) in dioxane:H2O (2:1; 15 mL) was added 4-bromo-1-fluoro-2-(methylsulfonyl)benzene (300 mg, 1.2 mmol, 1.0 eq., Apollo Scientific Ltd., Stockport, Cheshire, UK), K2CO3 (496 mg, 3.6 mmol, 2 eq.) and Pd(PPh3)4 (30 mg). The mixture was stirred under nitrogen at 140° C. in a microwave for 40 min. Solvent was evaporated and the residue was dissolved in DCM and washed with water. The DCM layer was dried and evaporated. Purification via column chromatography (eluent: PE:EA=3:1) yielded 400 mg (72%) of 3-(4-fluoro-3-(methylsulfonyl)phenyl)-4-methoxybenzaldehyde (27).

後処理

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water
  4. dry with materialThe DCM layer was dried
  5. customevaporated
  6. customPurification via column chromatography (eluent: PE:EA=3:1)

出典と根拠

ORDレコード
ord-45f4597c36274a5b985838bc77ac4440
出典データセット
uspto-grants-2014_09
特許番号
US08822467B2

関連ノート

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