Boron tribromide → 4-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one

HRID 1258270Notes

Reaction equation

HRID 1258270 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:24])[C:11](=[O:23])[N:12]([CH3:22])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]([CH3:24])[C:11](=[O:23])[N:12]([CH3:22])[C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 593548284,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one

Product 1

HCID 593547664-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred −40° C. solution of 4,5-bis(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one (0.6 g, 1.84 mmol) in DCM (10 mL), BBr3 (0.7 mL, 7.38 mmol) was added dropwise and the reaction mixture was then stirred for 48 h at RT, quenched with 6 N HCl and washed with water. The combined organic layers were then dried over Na2SO4, filtered and then concentrated in vacuo to afford 4-(4-hydroxyphenyl)-5-(4-methoxyphenyl)-1,3-dimethyl-1H-imidazol-2(3H)-one (0.38 mg, 66%) as a solid.

Workup

  1. customquenched with 6 N HCl
  2. washwashed with water
  3. dry with materialThe combined organic layers were then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-27d43f5e5cf64cfead0c9aa0880cff04
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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