Boron Trichloride → 4-Methoxy-5-methyl-2-nitrophenol

HRID 2354351Notes

Reaction equation

HRID 2354351 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 27780951,4-Dimethoxy-2-methyl-5-nitrobenzene

Product 1

HCID 574186644-Methoxy-5-methyl-2-nitrophenolYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

1-Methyl-2,5-bis(methyloxy)-4-nitrobenzene (3.96 g, 20 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to −20° C. A solution of BCl3 (1.0 M) in CH2Cl2 (20 mL) was added to above solution drop wise over 5 minutes. A purple solution was obtained. The reaction mixture was slowly warmed to room temperature and stirred for 20 h. The mixture was then quenched with saturated Na2CO3, stirred for 10 minutes and then extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was removed via rotovap to give the title compound (3.65 g, 99%) as a yellow solid. MS (ES) m/e 184 [M+H]+.

Workup

  1. customA purple solution was obtained
  2. temperatureThe reaction mixture was slowly warmed to room temperature
  3. customThe mixture was then quenched with saturated Na2CO3
  4. stirringstirred for 10 minutes
  5. extractionextracted with EtOAc (3×100 mL)
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was removed via rotovap

Sources & evidence

ORD record
ord-797535c02a53441781def30f7c9df803
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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