Trifluoroacetic acid → (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

HRID 555800Notes

Reaction equation

HRID 555800 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18]CC2C=CC(OC)=CC=2)=[CH:14][CH:13]=1)=[O:11].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59327033HCID 59327033, compound

Product 1

HCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of compound (1H-benzo[d]imidazol-2-yl)(4-(4-methoxybenzyloxy)phenyl)methanone (268 g, 0.75 mol) in dichloromethane (2.7 L) at ambient temperature was added TFA (289 mL, 3.75 mol, 5.0 eq.) slowly using an addition funnel. The reaction was stirred at ambient temp for 16 h. LCMS analysis of the reaction mixture revealed that the reaction was complete. The reaction mixture was neutralized with satd. aqueous NaHCO3 to pH=7-8, and stirred for 20 minutes. The resulting solid was filtered and washed with water and dried under vacuum oven at 45° C. to give product.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customdried under vacuum oven at 45° C.
  4. customto give product

Sources & evidence

ORD record
ord-bc7bcd987f2c40fbb9794d10d3de85be
Source dataset
uspto-grants-2011_11
Patent number
US08053438B2

Reaction notes

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