Carbon tetrabromide → HCID 57989229, compound

HRID 1689555Notes

Reaction equation

HRID 1689555 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:18][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 57989274HCID 57989274, compound

Product 1

HCID 57989229HCID 57989229, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 9-hydroxy-4,4-dimethylnonanoate (example 285, step f) (0.44 g) in DCM (19 mL) at 0° C. was treated with carbon tetrabromide (0.76 g) followed by triphenylphosphine (0.60 g) and the reaction mixture was stirred at room temperature overnight. Further amounts of carbon tetrabromide (0.76 g) and triphenylphosphine (0.60 g) were added and stirring continued for 3 hours. The solvent was removed by evaporation then the mixture was triturated with cyclohexane and the resultant solid removed by filtration. The solid was washed with cyclohexane and the filtrate was concentrated to about 15 mL and left to stand overnight. The solid which came out of solution was removed by filtration, washed with cyclohexane and the filtrate evaporated to afford the subtitled compound as a pale brown oil. Yield 0.56 g.

Workup

  1. stirringstirring
  2. waitcontinued for 3 hours
  3. customThe solvent was removed by evaporation
  4. customthe mixture was triturated with cyclohexane
  5. customthe resultant solid removed by filtration
  6. washThe solid was washed with cyclohexane
  7. concentrationthe filtrate was concentrated to about 15 mL
  8. waitleft
  9. waitto stand overnight
  10. customwas removed by filtration
  11. washwashed with cyclohexane
  12. customthe filtrate evaporated

Sources & evidence

ORD record
ord-1e62c01848894011ad5f731542fdeb61
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…