Potassium Carbonate → methyl 4-bromo-2-(1-methyl-1H-benzo[d]imidazol-5-yloxy)benzoate

HRID 573070Notes

Reaction equation

HRID 573070 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[N:4]=[CH:3]1.[Br:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15](F)[CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:21]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[N:2]([CH3:1])[CH:3]=[N:4][C:5]=3[CH:10]=2)[CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8404451-Methyl-1H-benzo[d]imidazol-5-olHCID 113453114-Bromo-2-fluoro-benzoic acid methyl ester

Product 1

HCID 67226311methyl 4-bromo-2-(1-methyl-1H-benzo[d]imidazol-5-yloxy)benzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-methyl-1H-benzo[d]imidazol-5-ol (296 mg), methyl 4-bromo-2-fluorobenzoate (311 mg) and potassium carbonate (553 mg) were combined in dimethylsulfoxide and heated to 90° C. overnight. The reaction mixture was diluted with ethyl acetate and washed thoroughly with water and with brine, dried over MgSO4, filtered and concentrated.

Workup

  1. washwashed thoroughly with water and with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-448a9e04a5114db490e4a384dfaf0d36
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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