Bromobenzene → 1-Methoxy-3-phenoxybenzene

HRID 1416948

반응식

HRID 1416948 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1.[Cu].S([O-])([O-])(=O)=O.[Cu+2]>[O:9]([C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 3

HCID 7961BromobenzeneHCID 90073-MethoxyphenolHCID 11430Potassium Carbonate

생성물 1

HCID 742521-Methoxy-3-phenoxybenzene수율 75%

시약·촉매·용매 3

HCID 23978Copper촉매HCID 24462Copper Sulfate촉매HCID 1049Pyridine용매

실험 절차

3-Methoxyphenol (287.4 g; 2.3 Mol), 316.0 g (2.0 Mol) of bromobenzene, 552 g (4.0 Mol) of K2CO3, 12.0 g (0.19 Mol) of activated copper (prepared according to Org. Syn. Coll. Vol. II, p 445-6), Cu(II) acetate hydrate 2.0 g (11 mMol), CuO powder (2.0 g; 25 mMol), and 2.0 g of copper sulfate (13 mMol) were combined in 1500 mL of dry pyridine. The resultant mixture was heated under reflux for 3 days. After cooling, the mixture was concentrated under reduced pressure, then treated with 6N HCl. Extraction was carried out with ether. The combined organics were washed with water, dilute NaOH, and water, then concentrated under reduced pressure. The residue was distilled in vacuo to give 3-phenoxyanisole, distilling at 138-40° C./2 mm pressure, 119 g (75% yield). H1NMR (CDCl3) d: 3.81 (s, 3 H), 6.61 (m, 2 H), 6.68 (d, J=7.8 Hz, 1 H), 7.06 (d, J=8.3, 2 H), 7.14 (t, J=7.4 Hz, 1 H), 7.25 (t, J=8.4 Hz, 1 H), 7.37 (t, J=7.8 Hz, 2 H).

후처리

  1. temperatureunder reflux for 3 days
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated under reduced pressure
  4. additiontreated with 6N HCl
  5. extractionExtraction
  6. washThe combined organics were washed with water, dilute NaOH, and water
  7. concentrationconcentrated under reduced pressure
  8. distillationThe residue was distilled in vacuo

출처 및 근거

ORD 기록
ord-7e67478c7d044f8e9f64de0d01dde074
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05916922

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