Potassium Phosphate, Tribasic → 5-Cyclopropyl-1,3-difluoro-2-nitrobenzene

HRID 447775

반응식

HRID 447775 반응식
Br[C:2]1[CH:3]=[C:4]([F:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Na+].[Br-]>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.C1(C)C=CC=CC=1>[CH:13]1([C:2]2[CH:3]=[C:4]([F:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([F:8])[CH:7]=2)[CH2:15][CH2:14]1

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 253881Sodium BromideHCID 2760897Cyclopropylboronic acidHCID 213354875-Bromo-1,3-difluoro-2-nitrobenzene

생성물 1

HCID 596832545-Cyclopropyl-1,3-difluoro-2-nitrobenzene수율 141%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
160 °C

실험 절차

5-bromo-1,3-difluoro-2-nitrobenzene (D24, 560 mg, 2.35 mmol), cyclopropylboronic acid (1 eq., 2.35 mmol, 0.2 g), K3PO4 (3 eq., 7.1 mmol, 1.50 g), NaBr (1 eq., 2.35 mmol, 0.24 g) and Pd(PPh3)4 (280 mg) were added to 3 ml of dry toluene and the mixture was heated by microwave at 160° C. for 40 minutes. The mixture was then poured onto water (10 ml) and extracted with ethyl acetate (3×20 ml). The combined organics were dried over MgSO4, filtered and the solvent was evaporated to afford 660 mg of brown crude product which was purified by silica gel chromatography (5-20% diethyl ether-40-60° petroleum ether) to afford the title compound as a yellow oil, 300 mg, 64%.

후처리

  1. additionThe mixture was then poured onto water (10 ml)
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-562985611e7a4cdeaa8c4734b214ebe1
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481566B2

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