1-Bromo-3-chloropropane → Methyl 4-(3-chloropropoxy)benzoate

HRID 265898Notes

Reaction equation

HRID 265898 reaction equation
C(N([CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)CC)C.[C:18]([O-])([O-])=O.[Cs+].[Cs+].BrCC[CH2:27][Cl:28]>CN(C=O)C>[Cl:28][CH2:27][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH3:18])=[O:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 134390874-[2-(Diethylamino)ethoxy]benzoic acid

Product 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Methyl 4-hydroxy benzoic acid (23-2) (Aldrich) (4.56 g, 30 mmol) in DMF (100 mL) was treated with Cs2CO3 (14.67 g, 45 mmol) at room temperature. After 0.5 hours, 3-bromo-1-chloropropane (5.94 mL, 60 mmol) was added and the solution was stirred for 4 hours. The reaction mixture was filtered and concentrated to give 27-1 as a white solid. Rf (10% EtOAc/hexanes) 0.36.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b33afc0ee22d41a7b71b588aad91ea48
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Reaction notes

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