Dimethylformamide → HCID 66876629, compound

HRID 871281Notes

Reaction equation

HRID 871281 reaction equation
CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16]([O:18][CH3:19])=[O:17].Br[CH2:26][CH2:27][Cl:28]>O>[Cl:28][CH2:27][CH2:26][O:12][C:13]1[CH:14]=[C:15]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-Chloroethane2×HCID 11430Potassium CarbonateHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Product 1

HCID 66876629HCID 66876629, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To DMF (40 mL) was added potassium carbonate (9.1 g, 65.9 mmol) and methyl 3-hydroxy-4-methoxybenzoate (10.0 g, 54.9 mmol) and the mixture stirred 30 minutes at room temperature 1-bromo-2-chloroethane (11.0 g, 76.8 mmol) was added and the mixture was heated at 60° C. overnight at which point excess 1-bromo-2-chloroethane (5.5 g, 38.4 mmol) was added and heating continued for 8 hours. After cooling to room temperature, the mixture was diluted with H2O, filtered, and the solid washed with EtOAc to give methyl 3-(2-chloroethoxy)-4-methoxybenzoate (4.04 g, 16.6 mmol, 30%). 1H NMR (300 MHz, DMSO-d6) δ 7.63 (d, 1H), 7.47 (s, 1H), 7.11 (d, 1H), 4.29 (t, 2H), 3.95 (t, 2H), 3.86 (s, 3H), 3.81 (s, 3H); LC-MS (ESI) m/z 245 (M+H)+.

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureheating
  4. filtrationfiltered
  5. washthe solid washed with EtOAc

Sources & evidence

ORD record
ord-706b745e2efa41b2be171562ea8da10d
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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