Carbon tetrabromide → HCID 67406463, compound

HRID 714634Notes

Reaction equation

HRID 714634 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)[N:10]=[CH: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[N:10]=[CH: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 67409606HCID 67409606, compound

Product 1

HCID 67406463HCID 67406463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

48 mg (0.16 mmol) of the compound from Example 38A and 63 mg (0.24 mmol) of triphenylphosphine were dissolved in 1.6 ml of THF, and 80 mg (0.24 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 5:1, then 1:1). This gave 17 mg (39% 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 17 mg (39% of theory) of the target compound which was immediately reacted further

Sources & evidence

ORD record
ord-2df8df89fd444ba08d8dd0a5abac3095
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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