Dimethylformamide → 3-(3-Fluorophenyl)-5-fluorobenzoic acid

HRID 1771658노트

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HRID 1771658 반응식
[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]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:15]([OH:17])=[O:16].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.C(OCC)(=O)C.O>[F:21][C:19]1[CH:18]=[C:14]([CH:13]=[C:12]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[CH:7]=2)[CH:20]=1)[C:15]([OH:17])=[O:16]

참가 물질

9

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 27733393-Bromo-5-fluorobenzoic acid

생성물 1

HCID 463123233-(3-Fluorophenyl)-5-fluorobenzoic acid수율 90%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of 3-fluorophenyl boronic acid (0.7 g, 5.0 mmol, 1.0 eq), 3-bromo-5-fluoro-benzoic acid (1 g, 4.6 mmol, 1.1 eq) and Na2CO3 (1.45 g, 13.7 mmol, 3 eq) in a mixture of EtOH (5 mL), DMF (20 mL) and H2O (5 mL) under N2 was added Pd(PPh3)4 (200 mg, 0.17 mmol, 0.05 eq). The mixture was stirred at 100° C. overnight then cooled to room temperature. Water and ethyl acetate were added and the reaction was filtered through Celite and the aqueous layer was extracted with EtOAc. The organic extract was discarded and the aqueous layer was acidified to pH 4-5 by addition of 1M HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (970 mg, 90%).

후처리

  1. temperaturethen cooled to room temperature
  2. filtrationthe reaction was filtered through Celite
  3. extractionthe aqueous layer was extracted with EtOAc
  4. extractionThe organic extract
  5. additionthe aqueous layer was acidified to pH 4-5 by addition of 1M HCl
  6. extractionextracted with EtOAc
  7. washThe combined organic extracts were washed with water and brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-d2dae7b28f4a489c976efff54709bf8a
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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