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Potassium Carbonate → 2-Fluoro-5-(3-fluorophenyl)-3-methyl-benzoic acid

HRID 1771622
ノート
印刷プレビュー

反応式

HRID 1771622 の反応式
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.O1CCOCC1.C([O-])([O-])=O.[K+].[K+]>CCO.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.O>[F:11][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([F:13])[CH:19]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]
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

8

反応物 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27339863-Fluorophenylboronic acidHCID 814779685-Bromo-2-fluoro-3-methylbenzoic acid

生成物 1

HCID 894436582-Fluoro-5-(3-fluorophenyl)-3-methyl-benzoic acid収率 75.2%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

To a solution of 5-bromo-2-fluoro-3-methyl-benzoic acid (697 mg, 2.99 mmol, 1.0 eq) and (3-fluorophenyl)boronic acid (502 mg, 3.59 mmol, 1.2 eq) in a mixture of EtOH (10 mL), dioxane (20 mL) and H2O (10 mL) were added K2CO3 (142 mg, 1.03 mmol, 2.5 eq) and Pd(PPh3)4 (345 mg, 0.30 mmol, 0.1 eq). The mixture was heated at 85° C. overnight. The reaction was quenched by addition of 1M HCl and the aqueous phase extracted with EtOAc. The organic extract was dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by chromatography to give the title compound as a solid (558 mg, 73%).

後処理

  1. customThe reaction was quenched by addition of 1M HCl
  2. extractionthe aqueous phase extracted with EtOAc
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-3c288aa163a147aba797e6b333fa82bc
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249085B2

反応ノート

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