1-Bromo-3-chloropropane → HCID 19788728, compound

HRID 1656600Notes

Reaction equation

HRID 1656600 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CO>[Cl:19][CH2:18][CH2:17][CH2:16][O:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 19788728HCID 19788728, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirring solution of 4-(imidazol-1-yl)phenol (20. g, 125 mmol) and NaOH (5.0 g, 125 mmol) in methanol (600 mL) was added 1-bromo-3-chloropropane (49 mL, 500 mmol). The reaction was stirred for 18 hours at 70° C. under nitrogen, concentrated, and partitioned between 1.0 N NaOH/CH2Cl2The organic phase was dried and concentrated to afford crude product which was purified by HPLC (5% CH3OH/CH2Cl2) to give 6.0 g (20%) of 1-[4-(3-chloropropoxy)phenyl]-1H-imidazole as a brown solid: mp 53°-55° C.; 1H NMR (CDCl3): δ 7.80 (brs, 1H), 7.30 (m, 3H), 7.20 (bs, 1H), 4.16 (t, J=6.0 Hz, 2H), 3.76 (t, J=6.0 Hz, 2H), 2.30 (m, 2H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between 1.0 N NaOH/CH2Cl2The organic phase
  3. customwas dried
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by HPLC (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-bc4688eee49d44a5a5e5616d6b7825b3
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

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