Sodium hydride → HCID 67099800, compound

HRID 1868839Notes

Reaction equation

HRID 1868839 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[H-].[Na+].Cl[CH:16](Cl)[CH2:17][O:18][CH2:19][CH:20](Cl)Cl>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([C:9]([O:11][CH3:12])=[O:10])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 623831,1'-Oxybis(2,2-dichloroethane)HCID 2733230Methyl 2-fluorophenylacetate

Product 1

HCID 67099800HCID 67099800, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-bath cooled, stirred solution of methyl 2-(2-fluorophenyl)acetate (3.4 g, 20 mmol) in THF (100 mL) was added NaH (1.8 g, 44 mmol). The reaction was stirred at 0° C. for 10 minutes and then dichloroethyl ether (2.7 mL, 22 mmol) and tetrabutylammonium bromide (0.33 g, 1.0 mmol) were added sequentially. The yellow reaction mixture was stirred for 16 hours at room temperature and then quenched with a saturated ammonium chloride solution. The aqueous layer was extracted with EtOAc (3×60 mL), and the organic layers were combined, dried (Na2SO4), filtered and concentrated to afford a yellow oil. Purification by flash chromatography (100% DCM) provided a pale yellow oil (2.5 g). MS m/e=239.0 (M+H)+.

Workup

  1. temperatureTo an ice-bath cooled
  2. stirringThe yellow reaction mixture was stirred for 16 hours at room temperature
  3. customquenched with a saturated ammonium chloride solution
  4. extractionThe aqueous layer was extracted with EtOAc (3×60 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a yellow oil
  9. customPurification by flash chromatography (100% DCM)

Sources & evidence

ORD record
ord-0ce22c459a074c95835504cac870d7b7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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