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

HRID 1771806노트

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HRID 1771806 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

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온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-06d61654a77e481a98f85b91852f8995
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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