Benzyl Bromide → 2-(Benzyloxy)-1,3-dichloro-5-nitrobenzene

HRID 883816

Reaction equation

HRID 883816 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:12]([Cl:19])[C:11]=1[OH:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:20][C:11]1[C:12]([Cl:19])=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:10]=1[Cl:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120662,6-Dichloro-4-nitrophenol

Product 1

HCID 595097642-(Benzyloxy)-1,3-dichloro-5-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
75 °C

Procedure

Benzyl bromide (17.25 mL, 144 mmol) was added to a stirring solution of 2,6-dichloro-4-nitrophenol (5 g, 24 mmol) and potassium carbonate (13.3 g, 96 mmol) in acetone (30 mL). The mixture was heated to 75° C. for 12 h before being cooled to room temperature and poured into ice-water (100 mL). The mixture was extracted with chloroform (200 mL), washed with brine (100 mL) and the combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (9:1, hexane/dichloromethane) to afford 2-(benzyloxy)-1,3-dichloro-5-nitrobenzene as a white solid (99% yield).

Workup

  1. temperaturebefore being cooled to room temperature
  2. extractionThe mixture was extracted with chloroform (200 mL)
  3. washwashed with brine (100 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (9:1, hexane/dichloromethane)

Sources & evidence

ORD record
ord-adf458a830bd4170b2b9a7d04b267dfc
Source dataset
uspto-grants-2012_08
Patent number
US08236984B2

Linked notes

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