Hydrogen Bromide → 1-[4-(4-Hydroxyphenyl)butyl]imidazole

HRID 1768037Notes

Reaction equation

HRID 1768037 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:5][CH:4]=1.Br.[OH-].[Na+]>>[N:13]1([CH2:12][CH2:11][CH2:10][CH2:9][C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 236145331-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazole

Product 1

HCID 220096641-[4-(4-Hydroxyphenyl)butyl]imidazole

Conditions

Temperature
0 °C

Procedure

1.90 g (8.25 mmol) 1-[4-(4-methoxy-phenyl)-butyl]-1H-imidazole and 28 ml (247 mmol) 48% aqueous hydrobromic acid were stirred at 80° C. for 10 h. The mixture was cooled to 0° C., 23 ml of 4 N NaOH added, extracted with toluene and the aqueous phase adjusted to pH=6.3 by addition of 6 N HCl. The resulting precipitate was isolated, washed with ethyl acetate/n-heptane 2:1 and dried. 1.2 g (67%) slightly yellow powder.

Workup

  1. extractionextracted with toluene
  2. additionthe aqueous phase adjusted to pH=6.3 by addition of 6 N HCl
  3. customThe resulting precipitate was isolated
  4. washwashed with ethyl acetate/n-heptane 2:1
  5. customdried

Sources & evidence

ORD record
ord-f3ef5c72d02b43eda97fd32d78b3a16d
Source dataset
uspto-grants-2007_06
Patent number
US07235574B2

Reaction notes

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