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

HRID 51571

Reaction equation

HRID 51571 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-f7c71ebe2db44a70b5b01be8c159771c
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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