Sodium Carbonate → 1-Bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane

HRID 637671Notes

Reaction equation

HRID 637671 reaction equation
B(Br)(Br)[Br:2].[Cl:5][C:6]1[C:7]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][C:9]([O:15]C)=[C:10]([CH2:12][CH2:13]O)[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[Br:2][CH2:13][CH2:12][C:10]1[CH:11]=[C:6]([Cl:5])[C:7]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:8][C:9]=1[OH:15]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 25134Boron tribromideHCID 202556442-[5-Chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol

Product 1

HCID 202556591-Bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.0 ml of boron tribromide are added dropwise over a period of approximately 5 minutes to a solution, cooled to 0°, of 2.70 g (10 mmole) of 2-[5-chloro-2-methoxy-4-(piperidin-1-yl)-phenyl]-ethanol in 70 ml of absolute methylene chloride. The reaction mixture is then stirred for a further 5 hours at room temperature, poured onto ice and the resulting suspension is adjusted to pH 6-7 with solid sodium carbonate and extracted with methylene chloride. The organic extracts are washed with water, combined, dried over sodium sulphate and concentrated in a vacuum rotary evaporator. Recrystallisation from petroleum ether yields 1-bromo-2-[5-chloro-2-hydroxy-4-(piperidin-1-yl)-phenyl]-ethane, melting point 115°-116°.

Workup

  1. additionpoured onto ice
  2. extractionextracted with methylene chloride
  3. washThe organic extracts are washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in a vacuum rotary evaporator
  6. customRecrystallisation from petroleum ether

Sources & evidence

ORD record
ord-8d60f351c2d94d509b9a6d0e1e0a8786
Source dataset
uspto-grants-1985_12
Patent number
US04558043

Reaction notes

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