Carbon tetrabromide → HCID 67411827, compound

HRID 714635Notes

Reaction equation

HRID 714635 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[C:11]([CH2:13]O)[CH:10]=[N:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C1COCC1>[Br:35][CH2:13][C:11]1[CH:10]=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67410414HCID 67410414, compound

Product 1

HCID 67411827HCID 67411827, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

61 mg (0.27 mmol) of the compound from Example 39A and 105 mg (0.40 mmol) of triphenylphosphine were dissolved in 1.6 ml of THF, and 132 mg (0.40 mmol) of carbon tetrabromide were added at RT. The mixture was then stirred at RT for 16 h. For work-up, the mixture was filtered through 20 g of kieselguhr, the filter residue was rinsed with ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1, then 5:1). This gave 30 mg (42% of theory) of the target compound which was immediately reacted further.

Workup

  1. filtrationFor work-up, the mixture was filtered through 20 g of kieselguhr
  2. washthe filter residue was rinsed with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified chromatographically on silica gel (mobile phase
  5. customThis gave 30 mg (42% of theory) of the target compound which was immediately reacted further

Sources & evidence

ORD record
ord-0d34e43b0de846889ceceb7d318ed803
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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