4-Bromophenol → 4-(3,3-Diphenylpropoxy)bromobenzene

HRID 965199Notes

Reaction equation

HRID 965199 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CS(O[CH2:14][CH2:15][CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:17]1([CH:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:15][CH2:14][O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 222382923,3-Diphenylpropyl methanesulfonate

Product 1

HCID 190760174-(3,3-Diphenylpropoxy)bromobenzeneYield 103.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromophenol (1.73 g, 10 mmol), 1-methanesulphonyloxy-3, 3-diphenylpropane (3.05 g, 10 mmol) and anhydrous potassium carbonate (2.07 g, 15 mmol) in acetonitrile (25 mL) is stirred and heated to reflux under nitrogen for 24 h. The reaction mixture is filtered, washed with acetone and the combined filtrate and washings are evaporated to dryness in vacuo. The residue is taken up in Et2O washed with successive portions of 5% aqueous NaOH and H2O, dried (Na2SO4), filtered and concentrated in vacuo to give an oily residue (3.8 g) which crystallizes upon standing: mp 70°-71° C.; 1H NMR (CDCl3) d 7.35-7.16 (m, 12H), 6.70 (d, 2H, J=8.98), 4.22 (t, 1H, J=7.9), 3.85 (t, 2H, J=6.), 2.54 (q, 2H). IR 1592, 1490, 1470, 1291 cm1 ; MS 366-368 (MH+, one Br); Anal. calc'd. for C21 H19Br O: C, 68.86, H, 4.95. Found C, 68.60, 5.18.

Workup

  1. temperatureheated
  2. temperatureto reflux under nitrogen for 24 h
  3. filtrationThe reaction mixture is filtered
  4. washwashed with acetone
  5. customthe combined filtrate and washings are evaporated to dryness in vacuo
  6. washwashed with successive portions of 5% aqueous NaOH and H2O
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8c3bf75591e443e94f478268a72c212
Source dataset
uspto-grants-1998_06
Patent number
US05773469

Reaction notes

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