Hydrochloric Acid → HCID 59558413, compound

HRID 1175174Notes

Reaction equation

HRID 1175174 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([OH:8])[CH:7]=1.[CH3:10][N:11]([CH3:15])[CH2:12][CH2:13]Cl.Cl.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CC(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:7]=1)[O:8][CH2:13][CH2:12][N:11]([CH3:15])[CH3:10]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 79012-Chloro-N,N-dimethylethylamineHCID 11430Potassium CarbonateHCID 183421Phenol, 5-bromo-2-fluoro-HCID 516892Sodium Bicarbonate

Product 1

HCID 59558413HCID 59558413, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-fluoro-phenol (5.0 g, 26.2 mmol), 2-Dimethylaminoethylchlorid×HCl (5.66 g, 39.3 mmol) and K2CO3 (11.0 g, 78.5 mmol) are suspended/dissolved in 260 ml dry acetone and stirred at room temperature for 72 hours. Addition of aqueous NaHCO3 solution and extraction into ethyl acetate yields a crude product which is further purified by chromatography on silica. 1H-NMR (400 MHz; DMSO-d6): 7.41 (d, 1H), 7.20 (dd, 1H), 7.08-7.14 (m, 1H), 4.15 (t, 2H), 2.63 (t, 2H), 2.22 (s, 6H). MS (m/z, ES+): 262 (MH+).

Sources & evidence

ORD record
ord-b7769240a20047b5b40395a4edab9df9
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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