Phosphorus pentachloride → HCID 86693069, compound

HRID 575037Notes

Reaction equation

HRID 575037 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([NH:9][C:10]2=O)[CH2:7]3)=[CH:4][C:3]=1[F:15].P(Cl)(Cl)(Cl)(Cl)[Cl:17]>C1(C)C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:12]=[C:11]2[C:5]([CH:6]3[CH2:14][CH:8]([N:9]=[C:10]2[Cl:17])[CH2:7]3)=[CH:4][C:3]=1[F:15]

Participants

5

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 866930678-Bromo-7-fluoro-2,3,4,5-tetrahydro-3,5-methano-1H-2-benzazepin-1-one

Product 1

HCID 86693069HCID 86693069, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Into a 20000-mL 4-necked round-bottom flask was placed a solution of 5-bromo-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6-trien-8-one (800 g, 2.96 mol, 1.00 equiv) in toluene (10000 mL), followed by the addition of PCl5 (1540 g, 7.40 mol, 2.50 equiv) in several batches at 25° C. over 1 hour. The resulting solution was heated to reflux for 5 hr, cooled to room temperature and diluted with 5000 mL of ether. The solids were collected by filtration and dissolved in 10000 mL of ether. The resulting mixture was washed with 5000 mL of ammonia (10%), dried over anhydrous sodium sulfate and concentrated under vacuum to afford 700 g (82%) of 5-bromo-8-chloro-4-fluoro-9-azatricyclo[8.1.1.0[2,7]]dodeca-2,4,6,8-tetraene as a white solid.

Workup

  1. customInto a 20000-mL 4-necked round-bottom flask was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 hr
  4. filtrationThe solids were collected by filtration
  5. dissolutiondissolved in 10000 mL of ether
  6. washThe resulting mixture was washed with 5000 mL of ammonia (10%)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9b92a8c9bb84440a8252b02ec2e52c8c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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