Hydrogen Bromide → 4-Hydroxy-4'-nitrobiphenyl

HRID 493512

Reaction equation

HRID 493512 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 111280794-Methoxy-4'-nitrobiphenyl

Product 1

HCID 1380784-Hydroxy-4'-nitrobiphenyl

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

4′-Methoxy-4-nitro-biphenyl (4.55 g, 19.8 mmol), prepared in the previous step, in a mixture of glacial acetic acid plus 65 mL of 48% HBr was heated at approximately 120° C. until the reaction was complete by TLC. The reaction was concentrated under reduced pressure and the residue partitioned between diethyl ether and water. The organic layer was separated, dried (Na2SO4) and the solvent removed under reduced pressure to give 4′-hydroxy-4-nitro-biphenyl.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue partitioned between diethyl ether and water
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b96104b8c75c422aacbc263d6a4065c5
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Linked notes

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