2-Bromophenol → 1-Bromo-2-(2-ethylphenoxy)benzene

HRID 253554Notes

Reaction equation

HRID 253554 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O)[CH3:2].[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].CCN(CC)CC>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 72442-BromophenolHCID 8471TriethylamineHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 574196131-Bromo-2-(2-ethylphenoxy)benzeneYield 31%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-ethylphenylboronic acid (4.50 g, 30 mmol), 2-bromophenol (3.54 g, 20 mmol), and Cu(OAc)2 (1.86 g, 10 mmol) in anhydrous CH2Cl2 (50 mL) were added activated 4 Å molecular sieves (˜0.5 g), followed by anhydrous Et3N (7.0 mL, 50 mmol). The resulting dark green solution was stirred at rt for 48 h. The solvent was removed under vacuum and the residue was triturated several times with ether (˜200 mL). The combined organic solutions were washed with satd aq NH4Cl, and 1 N aq HCl aqueous solution, and solvent was removed under vacuum to give a crude product. Flash column chromatography gave 1-bromo-2-(2-ethylphenoxy)benzene (1.72 g, 31%) as a clear oil; 1H NMR (CDCl3, 400 MHz) δ: 7.62 (dd, 1H), 7.28 (m, 1H), 7.22-7.08 (m, 3H), 6.96 (m, 1H), 6.78 (m, 2H), 2.64 (q, 2H), 1.22 (t, 3H); MS no ionization was observed.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated several times with ether (˜200 mL)
  3. washThe combined organic solutions were washed with satd aq NH4Cl, and 1 N aq HCl aqueous solution, and solvent
  4. customwas removed under vacuum
  5. customto give a crude product

Sources & evidence

ORD record
ord-43699f6428104e0ebb0068ca970a8f32
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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