Sodium Carbonate → 7-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic Acid

HRID 1361008ノート

反応式

HRID 1361008 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[C:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([OH:15])[C:8]([C:12]([OH:14])=[O:13])=[CH:9]3)=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)(=[O:18])[CH3:17]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 745032-Naphthalenecarboxylic acid, 7-bromo-3-hydroxy-HCID 37021224-Acetylphenylboronic acid

生成物 1

HCID 574570427-(4-Acetylphenyl)-3-hydroxynaphthalene-2-carboxylic Acid収率 81.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 180Acetone溶媒2 回HCID 962Water溶媒

実験手順

To 7-bromo-3-hydroxynaphthalene-2-carboxylic acid (100 mg, 0.37 mmol) (example 340) was added a solution of 4-acetylphenylboronic acid (92 mg, 0.56 mmol) in acetone (2.2 mL) followed by a solution of sodium carbonate (198 mg, 1.87 mmol) in water (3.3 mL). A suspension of palladium(II) acetate (4 mg, 0.02 mmol) in acetone (0.5 mL) was filtered and added to the above solution. The mixture was purged with N2 and stirred vigorously for 24 hours at room temperature. The reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL) and the precipitate was filtered off and rinsed with water (3×40 mL). The crude product was dissolved in acetone (25 mL) and dried with magnesium sulfate (1 h). Filtration followed by concentration furnished the title compound as a solid (92 mg). 1H-NMR (DMSO-d6): δ 12.60 (1H, bs), 8.64 (1H, s), 8.42 (1H, s), 8.08 (2H, d), 7.97 (2H, d), 7.92 (2H, m), 7.33 (1H, s), 2.63 (3H, s); HPLC-MS (Method (A): m/z: 307 (M+1); Rt=3.84 min.

後処理

  1. filtrationwas filtered
  2. additionadded to the above solution
  3. customThe mixture was purged with N2
  4. additionThe reaction mixture was poured into 1 N hydrochloric acid (aq.) (60 mL)
  5. filtrationthe precipitate was filtered off
  6. washrinsed with water (3×40 mL)
  7. dissolutionThe crude product was dissolved in acetone (25 mL)
  8. dry with materialdried with magnesium sulfate (1 h)
  9. filtrationFiltration
  10. concentrationfollowed by concentration

出典と根拠

ORDレコード
ord-cb16a0ff8bd14ee693e79a2700529384
出典データセット
uspto-grants-2011_02
特許番号
US07879893B2

反応ノート

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