1,1-Dibromoethane → HCID 10554120, compound

HRID 2110396Notes

Reaction equation

HRID 2110396 reaction equation
[Mg].[C:2]12([C:12]3[CH:26]=[C:25](Br)[CH:24]=[CH:23][C:13]=3[O:14][CH2:15][CH:16]3[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2.BrC(Br)C.Br[C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][CH:42]=1)[CH:39]=[C:38]([C:43]([O:45][CH3:46])=[O:44])[CH:37]=[CH:36]2.[Cl-].[NH4+]>[Cl-].[Zn+2].[Cl-].C1COCC1>[C:2]12([C:12]3[CH:26]=[C:25]([C:33]4[CH:34]=[C:35]5[C:40](=[CH:41][CH:42]=4)[CH:39]=[C:38]([C:43]([O:45][CH3:46])=[O:44])[CH:37]=[CH:36]5)[CH:24]=[CH:23][C:13]=3[O:14][CH2:15][CH:16]3[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]3)[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH2:3]1)[CH2:9]2

Participants

8

Reactant 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 5462224Magnesium2×HCID 10717062HCID 10717062, compound

Product 1

HCID 10554120HCID 10554120, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent5×

Conditions

Temperature
20 °C

Procedure

962 mg (39.6 mmol) of magnesium granules are wetted with a minimum of THF. A solution of 7.4 g (17.6 mmol) of 4-(2-adamantan-1-yl-4-bromophenoxymethyl)-2,2-dimethyl[1,3]dioxolane, 50 ml of THF and 300 μl (3.5 mmol) of dibromoethane is run dropwise into the suspension of magnesium. The reaction medium is heated at the reflux of the THF for 1 h 30 min and then brought back to 20° C. 5.1 g (37.6 mmol) of zinc chloride, dried and melted under vacuum beforehand, are added while keeping the temperature of the medium at 20° C., and then 50 ml of THF are added and the medium is stirred at 20° C. for 1 h 30 min. 10 g (37.6 mmol) of methyl 6-bromonaphthalene-2-carboxylate are added in small fractions while maintaining the temperature of the medium at 20° C., and then 300 mg of NiCl2/dppe complex and 50 ml of THF are added and the reaction medium is stirred at ambient temperature for 15 h. The reaction medium is then treated with a saturated ammonium chloride solution and extracted with ether. The organic phase is filtered, washed with water, and then dried and concentrated under reduced pressure. The residue obtained is then purified by chromatography on a silica column (elution being carried out with 70 heptane/30 dichloromethane).

Workup

  1. temperatureThe reaction medium is heated at the
  2. custombrought back to 20° C
  3. additionare added
  4. customat 20° C.
  5. temperaturewhile maintaining the temperature of the medium at 20° C.
  6. stirringthe reaction medium is stirred at ambient temperature for 15 h
  7. extractionextracted with ether
  8. filtrationThe organic phase is filtered
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customThe residue obtained
  13. customis then purified by chromatography on a silica column (
  14. washelution

Sources & evidence

ORD record
ord-1a8ce41e7b384ee48b4002ff4ea15860
Source dataset
uspto-grants-2009_04
Patent number
US07517907B2

Reaction notes

Loading…