1-(4-Bromophenyl)-1H-imidazole-5-methanol → HCID 18005593, compound

HRID 1782099Notes

Reaction equation

HRID 1782099 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[CH:9]2)=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]=[O:14])=[CH:11][N:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 688732331-(4-Bromophenyl)-1H-imidazole-5-methanol

Product 1

HCID 18005593HCID 18005593, compound

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(4-bromophenyl)-3H-imidazol-4-yl]-methanol (5) (500 mg, 2.0 mmol) in dry methylene chloride (30 mL) was added MnO2 (1.74 g, 20.0 mmol) and the resulting mixture stirred overnight at rt. The suspension was then filtered through Celite and the filtrate concentrated under reduced pressure to give 3-(4-bromophenyl)-3H-imidazole-4-carbaldehyde (6). MS (ES+): m/z 251/253 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=7.24 (d, J=8.7 Hz, 2H), 7.64 (d, J=8.7 Hz, 2H), 7.77 (s, 1H), 7.94 (s, 1H), 9.78 (s, 1H).

Workup

  1. filtrationThe suspension was then filtered through Celite
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-b1788e5ee98e4e9cbc69387c0824d955
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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