Carbon tetrabromide → HCID 67395877, compound

HRID 714646Notes

Reaction equation

HRID 714646 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[C:13]([CH2:15]O)[CH:12]=[CH:11][N:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:39]>C1COCC1>[Br:39][CH2:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:18])([F:17])[F:1])[CH:14]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67056312HCID 67056312, compound

Product 1

HCID 67395877HCID 67395877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

495 mg (1.96 mmol) of the compound from Example 61A and 615 mg (2.35 mmol) of triphenylphosphine were dissolved in 15 ml of THF, and 778 mg (2.35 mmol) of carbon tetrabromide were added at RT. After the addition had ended, the mixture was stirred ar RT for 16 h. For work-up, the mixture was filtered through 20 g of kieselguhr and the filtrate was concentrated under reduced pressure. The residue was purified chromatographically on silica gel (mobile phase: first cyclohexane/ethyl acetate 70:30, then ethyl acetate). This gave, in a purity of 90%, 149 mg (22% of theory) of the target compound, which were immediately reacted further.

Workup

  1. additionAfter the addition
  2. filtrationFor work-up, the mixture was filtered through 20 g of kieselguhr
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified chromatographically on silica gel (mobile phase
  5. customThis gave, in a purity of 90%, 149 mg (22% of theory) of the target compound, which were immediately reacted further

Sources & evidence

ORD record
ord-c349bd00839048d98bbe3cf67501adf6
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

Loading…