Hydrochloric Acid → 1-(4-Bromo-benzyloxy)-3-chloro-5-nitro-benzene

HRID 2358786Notes

Reaction equation

HRID 2358786 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+]([O-])=O)[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C.O.CCOC(C)=O.CCCCCC>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][O:20][C:6]2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=2)=[CH:17][CH:16]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 330981-Chloro-3,5-dinitrobenzeneHCID 701194-Bromobenzyl alcohol

Product 1

HCID 684604931-(4-Bromo-benzyloxy)-3-chloro-5-nitro-benzeneYield 55.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 193a (0.75 g, 3.7 mmol), 4-bromobenzyl alcohol (0.77 g, 4.1 mmol) and K2CO3 (0.64 g, 4.6 mmol) in DMF (15 ml) was heated at 110° C. for 23 hours. The reaction mixture was cooled to room temperature, diluted with H2O, acidified to pH 2 with 10% HCl, and then extracted with EtOAc. The extract washed with H2O and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound. The residue was treated with 50 mL of a mixture of n-hexane and EtOAc (3:1) and silica gel. After being stirred at room temperature for 30 minutes, the mixture was filtered through celite. The filtrate was evaporated and the resulting solid washed with i-Pr2O to give the title compound as a pale yellow crystals (0.70 g).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. filtrationthe mixture was filtered through celite
  8. customThe filtrate was evaporated
  9. washthe resulting solid washed with i-Pr2O

Sources & evidence

ORD record
ord-d1ac65fec6004b9d9c26cdaacd2b3691
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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