Hydrochloric Acid → 2-Biphenylol, 5-nitro-

HRID 352986Notes

Reaction equation

HRID 352986 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11]COC.[C:15]1(OB(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].Cl>COCCOC.C(O)C.C(OCC)(=O)C>[OH:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 110973452-Bromo-1-methoxymethoxy-4-nitrobenzene

Product 1

HCID 202782-Biphenylol, 5-nitro-

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

5.3 g (0.02 mole) of 2-bromo-1-methoxymethoxy-4-nitrobenzene from step B and 2.80 g (0.023 mole) of phenylboric acid were dissolved in 70 mL of 1,2-dimethoxyethane under argon. Then, 0.5 g (0.0005 mole) of tetrakis-(triphenylphosphine)palladium and 13 mL of 2 N potassium carbonate solution were added, and the reaction mixture was heated to 80° C. At the end of the reaction, the reaction mixture was poured into 100 mL of ethyl acetate and the organic phase was extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using petroleum ether/ethyl acetate (9:1). The product thus obtained was heated to 50° C. in a mixture of 40 mL of ethanol and 15 mL of a 2.9 M ethanolic hydrochloric acid solution. After neutralization with NaOH, the solvent was distilled off in a rotary evaporator, and the residue was purified by vacuum distillation. This gave 3.5 g (82% of the theoretical) of 2-hydroxy-5-nitrobiphenyl.

Workup

  1. customAt the end of the reaction
  2. extractionthe organic phase was extracted with dilute sodium hydroxide solution
  3. dry with materialdried with magnesium sulfate
  4. distillationThe solvent was distilled off in a rotary evaporator
  5. customthe residue was purified on silica gel
  6. customThe product thus obtained
  7. distillationAfter neutralization with NaOH, the solvent was distilled off in a rotary evaporator
  8. distillationthe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-10dcc98cf98846c3959f9cee9e635781
Source dataset
uspto-grants-2004_06
Patent number
US06749644B2

Reaction notes

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