3-Bromobenzyl bromide → 1-[(3-bromophenyl)methyl]-1H-imidazole-5-propanol

HRID 973949Notes

Reaction equation

HRID 973949 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.CN(C)C([N:14]1[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][O:22][Si](C)(C)C)[N:16]=[CH:15]1)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:16]2[C:17]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:18][N:14]=[CH:15]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 699793-Bromobenzyl bromideHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Product 1

HCID 150356691-[(3-bromophenyl)methyl]-1H-imidazole-5-propanolYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 250 parts of 1-bromo-3-bromomethylbenzene, 168.5 parts of N,N-dimethyl-4-[3-[(trimethylsilyl)oxy]propyl]-1H-imidazole-1-carboxamide and 869 parts of acetonitrile was refluxed for 18 hours. After cooling to 0° C., ammonia was bubbled through the reaction mixture for 5 min. The solvent was evaporated and the residue was stirred for 1 hour in 1700 ml of hydrochloric acid 1N. The mixture was extracted with ethyl acetate. The aqueous layer was basified with Na2CO3 (sat.) and reextracted with ethyl acetate (5×450 parts). The combined extracts were washed with water, dried, filtered and evaporated, yielding 210 parts (100%) of 1-[(3-bromophenyl)methyl]-1H-imidazole-5-propanol (interm. 1).

Workup

  1. customammonia was bubbled through the reaction mixture for 5 min
  2. customThe solvent was evaporated
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-94c0f80aa981442d9037134b965a85be
Source dataset
uspto-grants-1991_11
Patent number
US05066656

Reaction notes

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