Hydrochloric Acid → HCID 11635227, compound

HRID 900488Notes

Reaction equation

HRID 900488 reaction equation
[CH2:1]([O:4][C:5](=[O:24])[CH:6]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH:2]=[CH2:3].[H-].[Na+].Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1)=[O:30].Cl>C1COCC1.O>[CH2:10]([O:9][C:7](=[O:8])[C:6]([CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=1)=[O:30])([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=1)[C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[O:24])[CH:11]=[CH2:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74544-Bromophenacyl bromideHCID 24758Sodium hydrideHCID 11667301HCID 11667301, compound

Product 1

HCID 11635227HCID 11635227, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Diallyl-2-(3-trifluoromethylbenzyl)malonate (1.03 g, 3.01 mmol) in anhyd THF (20 mL) was added dropwise to a stirred suspension of sodium hydride (95%, 84 mg, 3.31 mmol) in anhyd THF (20 mL) at room temperature. The clear solution was stirred at room temperature for 30 min and then a solution of 2,4′-dibromoacetophenone (1.0 g, 3.61 mmol) in THF (10 mL) was added dropwise. The reaction mixture was warmed to 50° C. for 3 h (TLC control), cooled to room temperature and then water (10 mL) was added cautiously. The reaction mixture was acidified to pH 3 with 2 N hydrochloric acid and then extracted with ethyl acetate (3×30 mL). The combined extract was washed with water, sat'd aq NaCl, dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (10% ethyl acetate in heptane) afforded the title compound as a colorless oil (1.23 g)

Workup

  1. temperatureThe reaction mixture was warmed to 50° C. for 3 h (TLC control)
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. extractionThe combined extract
  5. washwas washed with water
  6. dry with materialdried over anhyd MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography (10% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-bad08d6c728a4e95a831dcf11150c01b
Source dataset
uspto-grants-2008_04
Patent number
US07358364B2

Reaction notes

Loading…