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

HRID 51571

반응식

HRID 51571 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 227362824-Bromo-2-methoxy-1-phenoxy-benzene수율 12%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f7c71ebe2db44a70b5b01be8c159771c
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713474B2

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