Potassium Carbonate → HCID 59558706, compound

HRID 1175173Notes

Reaction equation

HRID 1175173 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.Br[CH2:11][CH2:12][O:13][CH2:14]CBr.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([O:8][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 183421Phenol, 5-bromo-2-fluoro-HCID 516892Sodium Bicarbonate

Product 1

HCID 59558706HCID 59558706, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-fluoro-phenol (5.0 g, 26.2 mmol), 2-bromoethylether (2.71 ml, 28.8 mmol) and K2CO3 (4.4 g, 31.4 mmol) are mixed in 50 ml DMF and stirred at 50 C for 6 hours. Addition of aqueous NaHCO3 solution and extraction into ethyl acetate yields the title compound as viscous oil. 1H-NMR (400 MHz; DMSO-d6): 7.40 (d, 1H), 7.21 (dd, 1H), 7.08-7.14 (m, 1H), 4.21 (t, 2H), 3.66 (t, 2H), 3.30 (s, 3H). LC-MS (m/z, ES+): 248 (MH+), retention time: 3.02 mins (LC-MS method 3)

Sources & evidence

ORD record
ord-d87e5646cd914e19a2f877e2b7237fb7
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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