1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)benzamide

HRID 1710734Notes

Reaction equation

HRID 1710734 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:17][CH2:18][CH2:19][CH2:20]Br>CC(=O)CC>[Cl:17][CH2:18][CH2:19][CH2:20][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 650524-Hydroxybenzamide

Product 1

HCID 144071764-(3-Chloropropoxy)benzamideYield 87.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxybenzamide (5 g, 36.5 mmol, 1 eq), potassium carbonate (10.08 g, 72.9 mmol, 2 eq), 3-chloro-1-bromopropane (4.7 ml, 47.4 mmol, 1.3 eq) in butanone is stirred at reflux for 48 h. The solvent is then removed under vacuum and the residue is triturated in hexane and filtered. The solid is taken up in ethyl acetate and washed with a saturated solution of sodium hydrogencarbonate. The organic layer is dried over magnesium sulfate and concentrated to give 4-(3-chloropropoxy)benzamide ax54 (6.8 g) as a white solid.

Workup

  1. temperatureat reflux for 48 h
  2. customThe solvent is then removed under vacuum
  3. customthe residue is triturated in hexane
  4. filtrationfiltered
  5. washwashed with a saturated solution of sodium hydrogencarbonate
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-436bd3cd4e7244588bbf7266c35dfbf8
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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