5,6,7,8-Tetrahydro-2-naphthol → 1-Bromo-5,6,7,8-tetrahydro-2-naphthalenol

HRID 643899Notes

Reaction equation

HRID 643899 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

HCID 143055,6,7,8-Tetrahydro-2-naphtholHCID 67184N-bromobutanimide

Product 1

HCID 222787171-Bromo-5,6,7,8-tetrahydro-2-naphthalenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. washThe mixture is washed with water
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe crude material is purified via Biotage
  6. washeluting with 5-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-1ebb5123b4644fd49450b46042036ffb
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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