2-Bromoethanol → HCID 86679483, compound

HRID 1776525Notes

Reaction equation

HRID 1776525 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.Br[CH2:22][CH2:23][OH:24].C([O-])([O-])=O.[K+].[K+]>CC#N>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[N:16]([CH2:22][CH2:23][OH:24])[S:17]([CH3:20])(=[O:19])=[O:18])[C:9]([O:11][CH3:12])=[O:10])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 59443764HCID 59443764, compound

Product 1

HCID 86679483HCID 86679483, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl 3-(cyclopropylmethoxy)-4-(methylsulfonamido)benzoate (1 g, 3.34 mmol), 2-bromoethanol (0.835 g, 6.68 mmol), and K2CO3 (0.923 g, 6.68 mmol) in CH3CN (12 ml) was heated at 110° C. under microwave irradiation for 12 hours. After cooling the solvent was evaporated and the residue was dissolved in EtOAc and filtered; the solvent was evaporated and the residue was purified by flash chromatography (eluent: EtOAc/petroleum ether 1/1) to give methyl 3-(cyclopropylmethoxy)-4-(N-(2-hydroxyethyl)methylsulfonamido)benzoate as a light brown oil (0.764 g, 2.225 mmol, 66.6% yield, /ESI+ 365.9 [MNa]+).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. dissolutionthe residue was dissolved in EtOAc
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customthe residue was purified by flash chromatography (eluent: EtOAc/petroleum ether 1/1)

Sources & evidence

ORD record
ord-bf0f0b2d6e874e88aa296fdad535a015
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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