Boron tribromide → 2,3-di-(4-hydroxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole hydrobromide

HRID 2052680Notes

Reaction equation

HRID 2052680 reaction equation
B(Br)(Br)[Br:2].C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[CH2:28][CH2:27][CH2:26][N:16]3[C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=2)=[CH:9][CH:8]=1>C(Cl)Cl>[BrH:2].[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]3[CH2:28][CH2:27][CH2:26][N:16]3[C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12815562,3-bis(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

Product 1

HCID 203763762,3-di-(4-hydroxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 46.5 g (0.19 mol) of boron tribromide in about 240 ml of dry methylene chloride was added dropwise with stirring over a 90 minute period to a solution of 35.0 g (0.11 mol) of 2,3-di(4-methoxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole in 600 ml of dry methylene chloride maintained at -75° under a nitrogen atmosphere. The solution was then decanted and the remaining solid material was slurried with methylene chloride and water, collected by filtration and dried to give 2,3-di-(4-hydroxyphenyl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole hydrobromide.

Workup

  1. temperaturemaintained at -75° under a nitrogen atmosphere
  2. customThe solution was then decanted
  3. filtrationcollected by filtration
  4. customdried

Sources & evidence

ORD record
ord-26267b204a9547fa8e9a470db9040808
Source dataset
uspto-grants-1980_01
Patent number
US04186205

Reaction notes

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