Dimethylformamide → 3′,4-Difluoro[1,1′-biphenyl]-3-carboxaldehyde

HRID 1771806ノート

反応式

HRID 1771806 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[F:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].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:10][C:5]1[CH:4]=[CH:3][C:2]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=2)=[CH:9][C:6]=1[CH:7]=[O:8]

参加物

8

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 27339863-Fluorophenylboronic acid

生成物 1

HCID 463122473′,4-Difluoro[1,1′-biphenyl]-3-carboxaldehyde収率 34.1%

試薬・触媒・溶媒 3

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

反応条件

温度
100 °C

実験手順

To a stirred mixture of 5-bromo-2-fluoro-benzaldehyde (3.0 g, 14.8 mmol, 1 eq), (3-fluorophenyl)boronic acid (2.48 g, 17.7 mmol, 1.2 eq) and K2CO3 (4.13 g, 44.4 mmol, 3 eq) in a mixture of EtOH (30 mL), DMF (30 mL) and water (10 mL) under N2 was added Pd(PPh3)4 (1.71 g, 1.48 mmol, 0.1 eq). The reaction was heated at 100° C. for 3 h, then filtered through Celite. The filtrate was diluted with water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 300:1) to give the title compound as a yellow oil (1.1 g, 34%).

後処理

  1. filtrationfiltered through Celite
  2. additionThe filtrate was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by column chromatography (petroleum ether:EtOAc, 300:1)

出典と根拠

ORDレコード
ord-06d61654a77e481a98f85b91852f8995
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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