Boron tribromide → 1-(4-Hydroxybenzyl)imidazole

HRID 1279916Notes

Reaction equation

HRID 1279916 reaction equation
C[O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 578587N-p-methoxybenzylimidazole

Product 1

HCID 1938221-(4-Hydroxybenzyl)imidazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the compound of Step A (16.3 g, 86.1 mmole) in methylene chloride (860 ml) cooled to 5° C., was added boron tribromide (32.6 ml, 344.4 mmole) dropwise over 15 minutes. After 2 hours at 5° C., the reaction was quenched with methanol dropwise, evaporated to dryness, and redissolved in methanol, water, and methylene chloride. The pH was adjusted to 8.4 with sodium hydroxide. The organic layer was dried over sodium sulfate and evaporated to dryness to give N-p-hydroxybenzylimidazole (13.6 g, 91%) which was used without further purification:

Workup

  1. customthe reaction was quenched with methanol dropwise
  2. customevaporated to dryness
  3. dissolutionredissolved in methanol
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f367899625344eb3b0f79bca73627947
Source dataset
uspto-grants-2002_09
Patent number
US06448396B2

Reaction notes

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