Sodium Carbonate → HCID 17965980、化合物

HRID 1348887ノート

反応式

HRID 1348887 の反応式
Cl[C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl.C(O)C>[Cl:15][C:16]1[CH:21]=[C:20]([C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=2)[CH:19]=[CH:18][CH:17]=1

参加物

9

反応物 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 83343Methyl 2-chloro-4-nitrobenzoateHCID 2734323(3-Chlorophenyl)boronic acid

生成物 1

HCID 17965980HCID 17965980、化合物収率 99.4%

試薬・触媒・溶媒 4

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 2-chloro-4-nitrobenzoate (0.432 g, 2.0 mmol), 3-chlorophenylboronic acid (0.375 g, 2.4 mmol), trans-dichlorobis(tricyclohexylphosphine)-palladium (II) (0.074 g, 0.1 mmol), and sodium carbonate (0.64 g, 6.0 mmol) in a mixture of toluene (10 mL), dioxane (10 mL), and ethanol (2 mL) was heated to reflux for 12 hours, cooled to room temperature, diluted with ethyl acetate (10 mL), washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes to provide 0.58 g (99%) of the desired product. MS (DCI/NH3) m/z 309 (M+NH4)+; 1H NMR (CDCl3) δ 8.27-8.22 (m, 2H), 8.00 (dd, 1H), 7.41-7.34 (m, 3H), 7.23-7.18 (m, 1H), 3.72 (s, 3H).

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 1:10 ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-eba5564ff91749a7a04dedf78fcc2c06
出典データセット
uspto-grants-2007_05
特許番号
US07211595B2

反応ノート

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