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

HRID 68608

반응식

HRID 68608 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 218864351,4-Dioxane--water (1/1)용매

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온도
140 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-45f4597c36274a5b985838bc77ac4440
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822467B2

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