Triethylamine → 4-Bromo-1-methyl-2-phenoxybenzene

HRID 1778858Notes

Reaction equation

HRID 1778858 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([O:8][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 126484045-Bromo-2-methylphenol

Product 1

HCID 542867314-Bromo-1-methyl-2-phenoxybenzene

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-2-methylphenol (1.0 g), phenylboronic acid (1.30 g), Cu(OAc)2 (0.97 g), and triethylamine (2.98 mL) in dichloromethane (50 mL) was stirred for 4 days. The mixture was diluted with ethyl acetate, washed four times with 1M aqueous NaOH solution and once with brine, dried over Na2SO4, filtered, and concentrated. The crude product was chromatographed on silica gel using 2% ethyl acetate in hexanes to afford the title compound.

Workup

  1. washwashed four times with 1M aqueous NaOH solution
  2. dry with materialonce with brine, dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel using 2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6f1b778d47ee44d0a90a5bf0da19b7bc
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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