Carbon tetrabromide → HCID 67396627, compound

HRID 714641Notes

Reaction equation

HRID 714641 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:12][C:11]([CH2:13]O)=[CH: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[S:12][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67396082HCID 67396082, compound

Product 1

HCID 67396627HCID 67396627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg (0.74 mmol) of the compound from Example 52A and 291 mg (1.11 mmol) of triphenylphosphine were dissolved in 8 ml of THF, and 367 mg (1.11 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 113 mg of contaminated target product (32% pure, 17% of theory) which were 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 113 mg of contaminated target product (32% pure, 17% of theory) which were immediately reacted further

Sources & evidence

ORD record
ord-4415d962608e450e8fc7acb669782fb1
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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