Potassium Carbonate → 4-Bromo-1-methoxy-2-(3-trifluoromethoxy-propoxy)-benzene

HRID 1158475Notes

Reaction equation

HRID 1158475 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([OH:8])[CH:7]=1.[F:11][C:12]([F:26])([F:25])[O:13][CH2:14][CH2:15][CH2:16]OS(C(F)(F)F)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:9][CH3:10])=[C:6]([O:8][CH2:16][CH2:15][CH2:14][O:13][C:12]([F:26])([F:25])[F:11])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1422285-Bromo-2-methoxyphenolHCID 754063563-(Trifluoromethoxy)propyl trifluoromethanesulfonate

Product 1

HCID 686172254-Bromo-1-methoxy-2-(3-trifluoromethoxy-propoxy)-benzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromo-2-methoxy-phenol (1.20 g, 5.62 mmol), crude trifluoro-methanesulfonic acid 3-trifluoromethoxy-propyl ester (2.52 g, 6.74 mmol; purity of 74%) and anhydrous K2CO3 (1.18 g, 8.42 mmol) in MeCN (8 mL) is stirred in a sealed flask at room temperature overnight and then filtered. The combined filtrates are concentrated and the crude product is chromatographed over silica gel (eluent: toluene) to give the title compound as oil. TLC, Rf (toluene/AcOEt 10:1)=0.63. 1H-NMR (CDCl3): δ 2.25 (m, 2H), 3.87 (s, 3H), 4.13 (m, 2H), 4.23 (m, 2H), 6.79 (dd, 1H), 7.04 (d,1H), 7.09 (dd, 1H) ppm. 19F-NMR (CDCl3): zδ −60.7 ppm.

Workup

  1. filtrationfiltered
  2. concentrationThe combined filtrates are concentrated
  3. customthe crude product is chromatographed over silica gel (eluent: toluene)

Sources & evidence

ORD record
ord-5503b34dfe94442193835d2f94c18f9a
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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