Dimethylformamide → Methyl 2',4'-dichloro-6-hydroxy-(1,1'-biphenyl)-carboxylate

HRID 133706ノート

反応式

HRID 133706 の反応式
O[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.CN(C=[O:17])C.[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:4]1[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=[CH:2][C:3]=1[OH:17]

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 2734659(2,4-Dichlorophenyl)boronic acid2 回HCID 11346465Methyl 4-hydroxy-3-iodobenzoate

生成物 1

HCID 69309329Methyl 2',4'-dichloro-6-hydroxy-(1,1'-biphenyl)-carboxylate

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒2 回HCID 167845palladium(II) acetate触媒2 回HCID 8471Triethylamine溶媒2 回

反応条件

温度
100 °C

実験手順

5.6 g of methyl 4-hydroxy-3-iodobenzoate are introduced under argon into 50 ml of anhydrous DMF and then 4.2 g of 2,4-dichlorophenylboronic acid and 5.54 ml of triethylamine and then 240 mg of tri-orthotolylphosphine are added and the mixture is left under argon for 1 hour. 180 mg of palladium acetate are added and then the mixture is heated at 100° C. for 4 hours. 2 g of 2,4-dichlorophenylboronic acid, 5.54 ml of triethylamine, 120 mg of tri-orthotolylphoshine and 180 mg of palladium acetate are added and then the mixture is heated at 100° C. for 8 hours. It is concentrated under vacuum and the residue is taken up in AcOEt and then washed with 10% NH4OH solution. Extraction is carried out with AcOEt and the extract is washed with water and then with saturated NaCl solution. The residue is dried and then chromatographed on silica, eluting with a cyclohexane/AcOEt mixture (82/18; v/v), to give 3.4 g of the expected compound.

後処理

  1. temperaturethe mixture is heated at 100° C. for 8 hours
  2. concentrationIt is concentrated under vacuum
  3. washwashed with 10% NH4OH solution
  4. extractionExtraction
  5. washthe extract is washed with water
  6. customThe residue is dried
  7. customchromatographed on silica
  8. washeluting with a cyclohexane/AcOEt mixture (82/18; v/v)

出典と根拠

ORDレコード
ord-439f04e51ddc47fab0cdd8cdd0c18163
出典データセット
uspto-grants-2008_06
特許番号
US07390924B2

反応ノート

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