N-bromobutanimide → 8-Bromo-2-naphthol

HRID 399451Notes

Reaction equation

HRID 399451 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 41361878-Bromo-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 6138268-Bromo-2-naphtholYield 207.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In two side by side reactions, 8-bromo-2-tetralone (7.0 g, 31.25 mmol) and N-bromosuccinimide (5.84 g, 32.8 mmol) were combined in carbon tetrachloride and refluxed 45 min. The reactions were cooled, filtered through diatomaceous earth (Celite™), and combined for workup. The organic solution was washed with saturated aqueous sodium bicarbonate and brine followed by drying through phase separating filter paper (1PS) and concentrated to give 14.44 g (104% crude) of 8-bromo-2-naphthol as a brown solid which was suitable for further reaction. A sample dissolved in methylene chloride and treated with activated carbon, concentrated, and triturated with hexane had: mp 96°-100° C.; 1HNMR (250 MHz, CDCl3) δ 7.79-7.73 (m, 3H), 7.56 (d, J=4.5 Hz, 1H), 7.22-7.14 (m, 3H). HRMS m/e calculated for C10H7BrO: 221.9680. Observed m/e: 221.9664.

Workup

  1. temperaturerefluxed 45 min
  2. temperatureThe reactions were cooled
  3. filtrationfiltered through diatomaceous earth (Celite™)
  4. washThe organic solution was washed with saturated aqueous sodium bicarbonate and brine
  5. customby drying through phase
  6. customseparating
  7. filtrationfilter paper (1PS)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-eeb80a74b5b44e328c0941261c357d27
Source dataset
uspto-grants-1998_10
Patent number
US05821245

Reaction notes

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