Carbon tetrabromide → 1-(2,2-Dibromovinyl)-3-(2-ethylbutyl)cyclobutane

HRID 1912093Notes

Reaction equation

HRID 1912093 reaction equation
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([CH:27]([CH2:35][CH3:36])[CH2:28][CH:29]1[CH2:32][CH:31]([CH:33]=O)[CH2:30]1)[CH3:26].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:2][C:1]([Br:5])=[CH:33][CH:31]1[CH2:32][CH:29]([CH2:28][CH:27]([CH2:25][CH3:26])[CH2:35][CH3:36])[CH2:30]1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 866750513-(2-Ethylbutyl)cyclobutanecarbaldehyde

Product 1

HCID 866750521-(2,2-Dibromovinyl)-3-(2-ethylbutyl)cyclobutane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of carbon tetrabromide (27.0 g) in methylene chloride (27 mL) was added dropwise a solution of triphenylphosphine (42.8 g) in methylene chloride (85 mL) at ice temperature. The mixture was stirred at ice temperature for 20 min., and then to the mixture was added dropwise a solution of 3-(2-ethylbutyl)cyclobutanecarbaldehyde in methylene chloride at ice temperature. After stirring at ice temperature for 40 min., saturated aqueous sodium bicarbonate (250 mL) was added dropwise to the mixture. The aqueous layer was removed, and the organic layer was washed with water (50 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. To the residue were added hexane/chloroform=1/1 (100 mL), silica gel (50 g) and hexane (300 mL). The mixture was filtered and the filtrate was concentrated in vacuo. To the residue was added hexane (300 mL), and the mixture was filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: hexane) to give the title compound (9.78 g).

Workup

  1. stirringAfter stirring at ice temperature for 40 min.
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with water (50 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. additionTo the residue were added hexane/chloroform=1/1 (100 mL), silica gel (50 g) and hexane (300 mL)
  8. filtrationThe mixture was filtered
  9. concentrationthe filtrate was concentrated in vacuo
  10. additionTo the residue was added hexane (300 mL)
  11. filtrationthe mixture was filtered
  12. concentrationThe filtrate was concentrated in vacuo
  13. customThe resultant residue was purified by silica gel column chromatography (Eluent: hexane)

Sources & evidence

ORD record
ord-416f885bc4594bcc97abfe1239aeccbc
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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