Hydrogen Bromide → 3'-Nitro[1,1'-biphenyl]-2-ol

HRID 1249325Notes

Reaction equation

HRID 1249325 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1.Br>CC(O)=O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 13425547HCID 13425547, compound

Product 1

HCID 124650853'-Nitro[1,1'-biphenyl]-2-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methoxy-3'-nitrobiphenyl (9.00 g, 3.9 mmol) was heated at reflux with HOAc (50 mL) and 48% HBr (50 mL) for 8 h. The solution was then concentrated in vacuo, poured into ice-cold H2O (300 mL) and extracted with CH2Cl2. The organic layer was dried, evaporated and recrystallized (50% aq MeOH) to afford 2-hydroxy-3'-nitrobiphenyl as yellow needles; 6.12 g (73%); mp 99.5°-100° C.

Workup

  1. concentrationThe solution was then concentrated in vacuo
  2. additionpoured into ice-cold H2O (300 mL)
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was dried
  5. customevaporated
  6. customrecrystallized (50% aq MeOH)

Sources & evidence

ORD record
ord-195b4c388c584a76abe497e4d7c1ca1f
Source dataset
uspto-grants-1986_12
Patent number
US04631119

Reaction notes

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