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

HRID 871322Notes

Reaction equation

HRID 871322 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C=O)C>[Cl:24][CH2:23][CH2:22][CH2:21][O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 11623039Methyl 3-(3-chloropropoxy)-4-methoxybenzoateYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To DMF (80 mL) was added potassium carbonate (5.7 g, 41.1 mmol) and methyl 3-hydroxy-4-methoxybenzoate (5.0 g, 27.4 mmol). The mixture was cooled to 0° C. and 1-bromo-3-chloropropane (8.64 g, 57.9 mmol) in DMF (10 mL) was added dropwise over 30 minutes. The mixture was allowed to warm to room temperature overnight. After removing most of the DMF in vacuo, the remaining oil was diluted with H2O and filtered to give methyl 3-(3-chloropropoxy)-4-methoxybenzoate (6.65 g, 25.8 mmol, 94%). 1H NMR (300 MHz, DMSO-d6) δ 7.61 (d, 1H), 7.47 (s, 1H), 7.09 (d, 1H), 4.12 (t, 2H), 3.85 (s, 3H), 3.80 (s, 3H), 3.78 (t, 2H), 2.23-2.15 (m, 2H); LC-MS (ESI) m/z 259 (M+H)+.

Workup

  1. temperatureto warm to room temperature overnight
  2. customAfter removing most of the DMF in vacuo
  3. additionthe remaining oil was diluted with H2O
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ef0680047dd54c05992958c53239cc63
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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