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

HRID 1361008노트

반응식

HRID 1361008 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 180Acetone용매2회HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cb16a0ff8bd14ee693e79a2700529384
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879893B2

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