5,6,7,8-Tetrahydro-2-naphthol → 1-Bromo-5,6,7,8-tetrahydro-2-naphthalenol
Reaction equation
[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 5,6,7,8-tetrahydro-2-naphthol (2.50 g, 16.9 mmol) in DMF (5 mL), is added dropswise NBS (3.0 g, 16.9 mmol). The solution is stirred at room temperature for 18 h. The mixture is washed with water, extracted with CH2Cl2, dried over MgSO4 and concentrated. The crude material is purified via Biotage, eluting with 5-40% EtOAc/hexanes to afford 1-bromo-5,6,7,8-tetrahydronaphthalen-2-ol.
Workup
- washThe mixture is washed with water
- extractionextracted with CH2Cl2
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe crude material is purified via Biotage
- washeluting with 5-40% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-1ebb5123b4644fd49450b46042036ffb
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07700633B2
Reaction notes
Loading…