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Potassium Carbonate → Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate

HRID 1662545
ノート
印刷プレビュー

反応式

HRID 1662545 の反応式
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[C:17]([O:19][CH3:20])=[O:18])(=O)=O.[F:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].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:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[C:7]1[C:8]([C:17]([O:19][CH3:20])=[O:18])=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2734335(2,5-Difluorophenyl)boronic acidHCID 120175464-[[(Trifluoromethyl)sulfonyl]oxy]-1,3-benzenedicarboxylic acid dimethyl ester

生成物 1

HCID 57707138Dimethyl 2',5'-difluoro-1,1'-biphenyl-2,4-dicarboxylate収率 90.1%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6228Dimethylformamide溶媒
HCID 57417360Sodium chloride; water溶媒

反応条件

温度
90 °C

実験手順

To a stirred solution of dimethyl 4-(trifluoromethylsulfonyloxy)isophthalate 66.13B (1.00 g, 2.9 mmol) in DMF (5.8 mL) at 23° C. was added 2,5-difluorophenylboronic acid (0.69 g, 4.4 mmol) (commercially available from Aldrich), and potassium carbonate (1.2 g, 8.8 mmol). Tetrakis(triphenylphosphine)palladium (0.24 g, 0.20 mmol) was then added to the mixture. The mixture was heated to 90° C. and was stirred for 17 hours. The reaction was then cooled to room temperature, diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 83.27A as a colorless oil (0.800 g, 89% yield).

後処理

  1. temperatureThe reaction was then cooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-696275f4ae994c9ea96b7db3a8e45ccb
出典データセット
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08030354B2

反応ノート

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