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

HRID 447775

反応式

HRID 447775 の反応式
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

参加物

7

反応物 4

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

生成物 1

HCID 596832545-Cyclopropyl-1,3-difluoro-2-nitrobenzene収率 141%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
160 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-562985611e7a4cdeaa8c4734b214ebe1
出典データセット
uspto-grants-2013_07
特許番号
US08481566B2

関連ノート

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