Carbon tetrabromide → Isohexane ethyl acetate

HRID 884401Notes

Reaction equation

HRID 884401 reaction equation
C(OC(N1[CH2:12][CH:11]([CH:13]=O)[CH:10]2OC[C:17]([O:20][CH3:21])([O:18]C)[CH:9]12)=O)(C)(C)C.[C:22](Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClCCl.CCCC(C)C>[CH3:17][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12].[CH3:22][CH2:21][O:20][C:17]([CH3:9])=[O:18]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 76659872HCID 76659872, compound

Product 1

HCID 21882781Isohexane ethyl acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 78922-MethylpentaneSolvent

Conditions

Temperature
0 °C

Procedure

The aldehyde 9-1 (318.3 mg, 1.06 mmol) (see reference example 3) in 6 mL dichloromethane (DCM) was added dropwise to a solution of CBr4 (700 mg, 2.11 mmol) and Ph3P (1.10 g, 4.19 mmol) in 10 mL DCM, with cooling in an ice bath. After stirring at 0° C. for 2 h, the mixture was diluted with 30 mL iso-hexane and then filtered through a short Celite column. The column was washed with 20 mL i-hexane, followed by 3/1 i-hexane—DCM. The filtrate was concentrated in vacuo to give light yellow solids. Flash chromatography (silica, 3/1 i-hexane—EtOAc) gave compound 9-2 (339.5 mg, 70% yield).

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationfiltered through a short Celite column
  3. washThe column was washed with 20 mL i-hexane
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give light yellow solids

Sources & evidence

ORD record
ord-c47cfef0cdbc4a009a460792004612e3
Source dataset
uspto-grants-2012_08
Patent number
US08242119B2

Reaction notes

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