Potassium Carbonate → 3-(4-Bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol

HRID 912498Notes

Reaction equation

HRID 912498 reaction equation
I[CH2:2][CH2:3][CH2:4][OH:5].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([C:14]([F:17])([F:16])[F:15])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.O>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:2][CH2:3][CH2:4][OH:5])=[C:9]([C:14]([F:15])([F:16])[F:17])[CH:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 693903-Iodo-1-propanolHCID 142784o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Product 1

HCID 576575913-(4-Bromo-2-(trifluoromethyl)-phenoxy)propan-1-ol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Iodopropanol (11.23 g) was added to a mixture of 4-bromo-2-(trifluoromethyl)-phenol (15 g) and potassium carbonate (172 g) in acetonitrile (150 ml). The above mixture was refluxed for 4 hours then diluted with ethyl acetate (500 ml) and water (300 ml). Organic layer was seperated, dried over magnesium sulphate, solvent removed under reduced pressure to give expected product clean enough for use at the next step (18.6 g). 1H NMR (CDCl3) δ: 7.67 (d, 1H), 7.58 (dd, 1H), 6.90 (dd, 1H), 4.18 (t, 2H), 3.87 (q, 2H), 2.07 (tt, 2H).

Workup

  1. temperatureThe above mixture was refluxed for 4 hours
  2. customOrganic layer was seperated
  3. dry with materialdried over magnesium sulphate, solvent
  4. customremoved under reduced pressure

Sources & evidence

ORD record
ord-edfa05cf7218496383ea4f9e9e96e455
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

Loading…