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

HRID 1848836Notes

Reaction equation

HRID 1848836 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-8e1e64f70a1a4640bb13838365ed92de
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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