Triethylamine → 4-Bromo-2-methoxy-1-phenoxy-benzene

HRID 51571

反応式

HRID 51571 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[C:11]1(B(O)O)[CH:16]=[CH:15]C=[CH:13][CH:12]=1.[CH2:20](N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=2)=[C:4]([O:10][CH3:20])[CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 1422285-Bromo-2-methoxyphenol

生成物 1

HCID 227362824-Bromo-2-methoxy-1-phenoxy-benzene収率 12%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-bromoguaiacol (2.23 g, 11 mmol), phenyl boronic acid (4.03 g, 33 mmol), copper(II) acetate (2.18 g, 12 mmol) and 4A powdered molecular sieves (20 g) in dichloromethane (100 mL) was treated with triethylamine (5.5 g, 55 mmol) then stirred at ambient temperature for 20 hours. The mixture was filtered, concentrated under reduced pressure and purified by flash chromatography on silica gel using heptane/ethyl acetate (75:25) as an eluent to give 4-bromo-2-methoxy-1-phenoxybenzene (350 mg, 12%): 1H NMR (DMSO-d6, 400 MHz) δ 7.3-7.4(m, 3H), 7.15(d, 1H), 7.05(t, 1H), 6.98(d, 1H), 6.85 (d, 2H), 3.77(s, 3H); RP-HPLC (Hypersil HS, 5 μm, 100 A, 4.6×250 mm; 25%-100% acetonitrile—0.05 M ammonium acetate over 10 min, 1 ml/min) tr 13.12 min.

後処理

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-f7c71ebe2db44a70b5b01be8c159771c
出典データセット
uspto-grants-2004_03
特許番号
US06713474B2

関連ノート

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