2,3,5-Trimethylphenol → 1-[2-(4-Bromophenyl)ethoxy]-2,3,5-trimethylbenzene

HRID 33030

Reaction equation

HRID 33030 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=1[O:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 127692,3,5-TrimethylphenolHCID 13831TributylphosphineHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 674216101-[2-(4-Bromophenyl)ethoxy]-2,3,5-trimethylbenzeneYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-bromophenyl)ethanol (20.0 mL, 143 mmol), 2,3,5-trimethylphenol (31.1 g, 229 mmol), azodicarboxylic dipiperidide (72.1 g, 286 mmol) and tributylphosphine (88 mL; 357 mmol) in toluene (2.00 L) was heated to reflux for 2 h. The mixture was allowed to cool to rt. The mixture was filtered, washed with toluene and the solvents were partially removed under reduced pressure. The residue was diluted with Et2O and washed with aq. 1M NaOH (2×). The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:3) yielded the title compound (33.1 g, 73%). LC-MS: Rt=6.95.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationThe mixture was filtered
  4. washwashed with toluene
  5. customthe solvents were partially removed under reduced pressure
  6. additionThe residue was diluted with Et2O
  7. washwashed with aq. 1M NaOH (2×)
  8. dry with materialextracts were dried over MgSO4
  9. filtrationfiltered
  10. customthe solvents were removed under reduced pressure
  11. customPurification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:3)

Sources & evidence

ORD record
ord-cbe262c4c9014bdc9e0c5fefc4472d11
Source dataset
uspto-grants-2008_09
Patent number
US07427613B2

Linked notes

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