Phosphorus pentachloride → N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chloride

HRID 508711Notes

Reaction equation

HRID 508711 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[N:9]=[CH:10]/[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][N:9]=[C:10]([Cl:20])[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 900336584-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]aniline

Product 1

HCID 131733232N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chlorideYield 23%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of (2E)-1-(4-bromophenyl)-2-(2-chloro-6-fluorobenzylidene)hydrazine (0.300 g, 1.32 mmol) in benzene (10 mL) was added PCl5 (0.330 g, 1.58 mmol). The reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with NaHCO3 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.110 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.17 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.7 Hz, 3H), 7.45-7.61 (m, 2H), 10.26 (s, 1H). MS (m/z): 361.34 (M−H)−.

Workup

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b2edc6d26a5453f91b3692a8370b870
Source dataset
uspto-grants-2015_08
Patent number
US09096545B2

Reaction notes

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