2,3-Dichloropropene → HCID 13911479, compound

HRID 2051246Notes

Reaction equation

HRID 2051246 reaction equation
[CH2:1]([Li])CCC.Br[C:7]1[C:19]([F:20])=[C:18]([F:21])[C:10]([CH2:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:15][O:14]2)=[C:9]([F:22])[C:8]=1[F:23].Cl[CH2:25][C:26]([Cl:28])=[CH2:27].[Cl-].[NH4+]>O1CCCC1.O>[Cl:28][C:26](=[CH2:27])[CH2:25][C:7]1[C:8]([F:23])=[C:9]([F:22])[C:10]([CH2:11][O:12][CH:13]2[CH2:17][CH2:16][CH2:1][CH2:15][O:14]2)=[C:18]([F:21])[C:19]=1[F:20]

Participants

7

Reactant 4

HCID 65652,3-DichloropropeneHCID 25517Ammonium ChlorideHCID 198331162-[4-Bromo-2,3,5,6-tetrafluorobenzyloxy]tetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 13911479HCID 13911479, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

n-Butyllithium (2.5 M in hexane, 2.3 cm3) was added portionwise to a solution of 2-[4-bromo-2,3,5,6-tetrafluorobenzyloxy]tetrahydrofuran (1.7 g) in dry tetrahydrofuran (10 cm3) under an atmosphere of dry nitrogen, whilst the reaction temperature was maintained between -30° C. and -20° C. After 15 minutes, copper (I) bromide-dimethyl sulphide complex (1.2 g) was added in one portion and the reaction temperature was maintained at -10° C. for 1 hour, after which time 1,2-dichloroprop-2-ene (1 cm3) was added, the reaction temperature then being allowed to warm to +15° C. After 3 hours, water followed by saturated aqueous ammonium chloride solution was added to the reaction mixture, which was then extracted into diethyl ether. The organic layer was then washed with water and brine, dried, and the solvent evaporated under reduced pressure. The residue was then subjected to medium pressure column chromatography on a silica gel column using a Gilson apparatus, eluting with petroleum ether (boiling range 30°-40° C.) containing diethyl ether (10% by volume) to give 2-[4-(2-chloroprop-2-en-1-yl)-2,3,5,6-tetrafluorobenzyloxy]tetrahydropyran (1.5 g).

Workup

  1. temperaturewas maintained between -30° C. and -20° C
  2. additioncopper (I) bromide-dimethyl sulphide complex (1.2 g) was added in one portion
  3. temperatureto warm to +15° C
  4. waitAfter 3 hours
  5. additionwas added to the reaction mixture, which
  6. extractionwas then extracted into diethyl ether
  7. washThe organic layer was then washed with water and brine
  8. customdried
  9. customthe solvent evaporated under reduced pressure
  10. washeluting with petroleum ether (boiling range 30°-40° C.)
  11. additioncontaining diethyl ether (10% by volume)

Sources & evidence

ORD record
ord-d211b60b646e484d849841b27bee0bf1
Source dataset
uspto-grants-1991_05
Patent number
US05017606

Reaction notes

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