Bromobenzene → 1-Methoxy-3-phenoxybenzene

HRID 1416948

反応式

HRID 1416948 の反応式
[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

参加物

7

反応物 3

HCID 7961BromobenzeneHCID 90073-MethoxyphenolHCID 11430Potassium Carbonate

生成物 1

HCID 742521-Methoxy-3-phenoxybenzene収率 75%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 24462Copper Sulfate触媒HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7e67478c7d044f8e9f64de0d01dde074
出典データセット
uspto-grants-1999_06
特許番号
US05916922

関連ノート

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