Carbon tetrabromide → HCID 67396375, compound

HRID 714666Notes

Reaction equation

HRID 714666 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[C:12]([CH2:14]O)[CH:11]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:40]>C1COCC1>[Br:40][CH2:14][C:12]1[CH:11]=[C:10]([C:16]([O:18][CH3:19])=[O:17])[CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[CH:13]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67396163HCID 67396163, compound

Product 1

HCID 67396375HCID 67396375, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

187 mg (0.68 mmol) of the compound from Example 111A and 266 mg (1.01 mmol) of triphenyl-phosphine were dissolved in 6 ml of THF, and 336 mg (1.01 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 cake was washed with ethyl acetate and the filtrate was concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3). This gave 275 mg (>100% of theory) of the target compound, which were immediately reacted further.

Workup

  1. filtrationFor work-up, the mixture was filtered through 20 g of kieselguhr
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified chromatographically on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3)
  5. customThis gave 275 mg (>100% of theory) of the target compound, which were immediately reacted further

Sources & evidence

ORD record
ord-9d91c5abde364f4b8f445ea88d5a15cc
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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