Sodium Carbonate → 4'-Chloro-2-nitro-1,1'-biphenyl

HRID 1791114ノート

反応式

HRID 1791114 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C(O)C.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>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 113411-Bromo-2-nitrobenzeneHCID 742994-Chlorophenylboronic acid

生成物 1

HCID 2355494'-Chloro-2-nitro-1,1'-biphenyl収率 86.5%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-bromonitrobenzene (646 mg) in THF (17 ml) under nitrogen was added tetrakis(triphenylphosphine)palladium (0) (900 mg). The resulting mixture was stirred at room temperature for 20 min, then a solution of 4-chlorophenylboronic acid (1.0 g) in ethanol (17 ml) was added and the resulting mixture stirred at room temperature for 1 hr. 2M sodium carbonate (17 ml) was then added and the reaction heated to reflux for 2 hrs. The mixture was then allowed to cool and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 ml) and the aqueous layer removed. The organic phase was washed with brine (20 ml), dried (magnesium sulfate), filtered and concentrated. The reside was purified by flash chromatography (0–10% ethyl acetate/hexane) to afford the sub-title compound as a yellow solid (646 mg): 1H NMR (400 MHz, CDCl3) δ 7.24–7.31 (2H, m), 7.41–7.47 (3H, m), 7.52 (1H, m), 7.65 (1H, m), 7.90 (1H, d).

後処理

  1. stirringthe resulting mixture stirred at room temperature for 1 hr
  2. temperaturethe reaction heated
  3. temperatureto reflux for 2 hrs
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in ethyl acetate (100 ml)
  7. customthe aqueous layer removed
  8. washThe organic phase was washed with brine (20 ml)
  9. dry with materialdried (magnesium sulfate)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe reside was purified by flash chromatography (0–10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-edf9fdfcefd14954ae03271d59898a8b
出典データセット
uspto-grants-2006_07
特許番号
US07074782B2

反応ノート

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