N-bromobutanimide → 8-Bromo-2-naphthol

HRID 1276194Notes

Reaction equation

HRID 1276194 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 (1 PS) 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, 3 H), 7.56 (d, J=4.5 Hz, 1 H), 7.22-7.14 (m, 3 H). 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 (1 PS)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f51461da74624d2c9cd853d564eefb3d
Source dataset
uspto-grants-2000_12
Patent number
US06166020

Reaction notes

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