Hydrogen Bromide → 4-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol

HRID 750945Notes

Reaction equation

HRID 750945 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]=[C:14]2[CH2:18][CH2:19][OH:20])=[CH:5][CH:4]=1.Br.[OH-].[Na+]>>[OH:20][CH2:19][CH2:18][C:14]1[N:13]([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]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 236145362-{1-[4-(4-Methoxy-phenyl)-butyl]-1H-imidazol-2-yl}-ethanol

Product 1

HCID 222593234-[4-[2-(2-hydroxyethyl)-1H-imidazol-1-yl]butyl]phenol

Conditions

Temperature
0 °C

Procedure

2.40 g (8.75 mmol) 2-{1-[4-(4-methoxy-phenyl)-butyl]-1H-imidazol-2-yl}-ethanol and 9 ml (81 mmol) 48% aqueous hydrobromic acid were stirred at 80° C. for 12 h. The mixture was cooled to 0° C., 23 ml 4 N NaOH added, extracted with toluene and the aqueous phase adjusted to pH=6.3 by addition of 1 N HCl. The resulting precipitate was isolated, washed twice with water and ethyl acetate and dried. 1.71 g (75%) yellow crystals.

Workup

  1. extractionextracted with toluene
  2. additionthe aqueous phase adjusted to pH=6.3 by addition of 1 N HCl
  3. customThe resulting precipitate was isolated
  4. washwashed twice with water and ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-bf431183484847da9c2f1fe71a4426ca
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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