Dimethylformamide → 5-(3-Fluorophenyl)-2-methoxy-3-methyl-benzoic acid

HRID 1771695ノート

反応式

HRID 1771695 の反応式
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.Br[C:12]1[CH:13]=[C:14]([CH3:23])[C:15]([O:21][CH3:22])=[C:16]([CH:20]=1)[C:17]([OH:19])=[O:18].C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>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:1][C:2]1[CH:3]=[C:4]([C:12]2[CH:13]=[C:14]([CH3:23])[C:15]([O:21][CH3:22])=[C:16]([CH:20]=2)[C:17]([OH:19])=[O:18])[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 9619195-Bromo-2-methoxy-3-methylbenzoic acidHCID 27339863-Fluorophenylboronic acid

生成物 1

HCID 894437175-(3-Fluorophenyl)-2-methoxy-3-methyl-benzoic acid収率 86%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

To a solution of 3-fluorophenylboronic acid (0.75 g, 5.39 mmol, 1.1 eq), 5-bromo-2-methoxy-3-methyl-benzoic acid (1.2 g, 4.90 mmol, 1.0 eq) and Na2CO3 (1.56 g, 14.69 mmol, 3 eq) in a mixture of EtOH (6 mL), DMF (24 mL) and H2O (6 mL) was added Pd(PPh3)4 (300 mg, 0.26 mmol, 0.05 eq). The mixture was stirred at 100° C. overnight. Water was added, the reaction was filtered and the filtrate was extracted with EtOAc. The organic extract was discarded and the aqueous phase was acidified to pH 4-5 with 1M HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to provide the title compound as a white solid (1.09 g, 86%).

後処理

  1. filtrationthe reaction was filtered
  2. extractionthe filtrate was extracted with EtOAc
  3. extractionThe organic extract
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-4f83e560718b4adc9e29f6f73db1b870
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

読み込み中…