Carbon tetrabromide → HCID 67406907, compound

HRID 714640Notes

Reaction equation

HRID 714640 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH2:13]O)=[CH:11][N:12]=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:10]1[O:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67407924HCID 67407924, compound

Product 1

HCID 67406907HCID 67406907, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

181 mg (0.77 mmol) of the compound from Example 50A and 242 mg (0.92 mmol) of triphenyl-phosphine were dissolved in 4 ml of THF, and 306 mg (0.92 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 by preparative HPLC [Method 19]. This gave 112 mg (42% of theory) of the target compound in a purity of 80% 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 by preparative HPLC [Method 19]
  5. customThis gave 112 mg (42% of theory) of the target compound in a purity of 80% which were immediately reacted further

Sources & evidence

ORD record
ord-4e86bdc72ae2418ea14b515813e0a2e4
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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