Phosphorus tribromide → 1-[4-(Bromomethyl)-3-chlorophenyl]-4-ethylpiperazine

HRID 577031Notes

Reaction equation

HRID 577031 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1[CH2:16]O.P(Br)(Br)[Br:19]>ClCCl>[Br:19][CH2:16][C:3]1[CH:4]=[CH:5][C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH3:15])[CH2:10][CH2:9]2)=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 23330426HCID 23330426, compound

Product 1

HCID 595894741-[4-(Bromomethyl)-3-chlorophenyl]-4-ethylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-chloro-4-(4-ethylpiperazin-1-yl)phenyl]methanol was dissolved in dichloromethane (30 mL) at 0° C. under nitrogen. Phosphorus tribromide (4.2 mL, 42 mmol) was added dropwise. The resulting mixture was stirred at room temperature for 2 hours. The reaction was quenched by addition of 10% NaHCO3 solution (5 mL). After 10 minutes, Na2SO4 (30 g) was added. The solvent was filtered and evaporated to provide 1-[4-(bromomethyl)-3-chlorophenyl]-4-ethylpiperazine, which was used without further purification.

Workup

  1. customThe reaction was quenched by addition of 10% NaHCO3 solution (5 mL)
  2. waitAfter 10 minutes
  3. additionNa2SO4 (30 g) was added
  4. filtrationThe solvent was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-e816bc723ad14f94b5a5d8dbe1c20597
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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