Hydrogen Bromide → 3'-Nitro-[1,1'-biphenyl]-2-ol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe solution was then concentrated in vacuo
- additionpoured into ice-cold H2O (300 mL)
- extractionextracted with CH2Cl2
- customThe organic layer was dried
- customevaporated
- 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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