Hydrochloric Acid → alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

HRID 232310Notes

Reaction equation

HRID 232310 reaction equation
Br.[Br:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:8][CH:7]=1)=[O:5].C([BH3-])#N.[Na+].CN(C1C=CC(N=NC2C=CC(S(O)(=O)=O)=CC=2)=CC=1)C.Cl>CO>[Br:2][CH2:3][CH:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[CH:10][CH:11]=1)[OH:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11037Benzenesulfonic acid, 4-(2-(4-(dimethylamino)phenyl)diazenyl)-HCID 5003444Sodium cyanoborohydrideHCID 200313102-Bromo-1-[4-(1H-imidazol-1-yl)phenyl]ethanone hydrobromide

Product 1

HCID 20031362alpha-(Bromomethyl)-4-(1H-imidazol-1-yl)benzenemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Stir a mixture of 2-bromo-1-[4-(1H-imidazol-1-yl)-phenyl]ethanone hydrobromide (15.45 g, 44.6 mmol) and sodium cyanoborohydride (5.61 g, 89.3 mmol) in methanol (250 mL). Add a crystal of methyl orange and adjust the pH to 3.0 with 1.35M hydrochloric acid in methanol. Maintain the pH at 3.0 for about 2 hr. Treat the resulting solution with decolorizing carbon and filter through celite. Concentrate the filtrate and add water (200 mL) and methylene chloride (100 mL) to the residue. Adjust the pH to 7.5 with 2N NaOH solution. Separate the layers and extract the aqueous layer with methylene chloride (100 mL) and combine, dry over Na2SO4, filter and concentrate in vacuo. Add ethyl acetate to the residue to afford crystals of the title compound.

Workup

  1. temperatureMaintain the pH at 3.0 for about 2 hr
  2. additionTreat the resulting solution with decolorizing carbon
  3. filtrationfilter through celite
  4. concentrationConcentrate the filtrate
  5. additionadd water (200 mL) and methylene chloride (100 mL) to the residue
  6. customSeparate the layers
  7. extractionextract the aqueous layer with methylene chloride (100 mL)
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-4f7dcaa715774f9f894b866d61c454e1
Source dataset
uspto-grants-1989_07
Patent number
US04851526

Reaction notes

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