Dimethylformamide → 7-(4-bromobutoxy)-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one

HRID 2074432

Reaction equation

HRID 2074432 reaction equation
CN(C)C=O.[OH:6][C:7]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]2[C:10]([C:11]([C:21]([F:24])([F:23])[F:22])=[CH:12][C:13](=[O:20])[O:14]2)=[CH:9][CH:8]=1.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>O>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][O:6][C:7]1[C:16]([CH2:17][CH2:18][CH3:19])=[C:15]2[C:10]([C:11]([C:21]([F:24])([F:22])[F:23])=[CH:12][C:13](=[O:20])[O:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 537014304-Trifluoromethyl-8-propyl-7-hydroxycoumarin

Product 1

HCID 579630147-(4-bromobutoxy)-8-propyl-4-(trifluoromethyl)-2H-chromen-2-oneYield 105.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An N,N-dimethylformamide (5 mL) solution of 7-hydroxy-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one (500 mg, 1.84 mmol), 1,4-dibromobutane (2.19 mL, 18.36 mmol), and potassium carbonate (375 mg, 2.76 mmol) was stirred overnight at room temperature. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The obtained residue was purified using silica-gel chromatography (hexane:ethyl acetate=10:1), and the title compound (0.79 g) was obtained as yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe obtained residue was purified

Sources & evidence

ORD record
ord-57a940b758594132aef2836b23d3e696
Source dataset
uspto-grants-2011_04
Patent number
US07919509B2

Linked notes

Loading…