Water → 6-Bromo-1-chloronaphthalen-2-ol

HRID 1373877Notes

Reaction equation

HRID 1373877 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.S(Cl)([Cl:16])(=O)=O.O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([Cl:16])=[C:7]([OH:12])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 220481596-Bromo-1-chloronaphthalen-2-olYield 48.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-bromo-2-naphthol (20.0 g, 89.7 mmol) and sulfuryl chloride (14.4 mL, 180 mmol) in chloroform (220 mL) was refluxed for 30 minutes. It was then stirred, while cooling to ambient temperature, for one hour. Water (100 mL) was added to the reaction mixture. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and solvent evaporated. The residue was recrystallized in hot hexane. It was rinsed with cold acetone and dried in vacuo at 60° C. for 30 minutes to yield 6-bromo-1-chloro-naphthalen-2-ol as a tan solid (11.2 g, 48.3%): MP: 100–1° C.; Mass spectrum (−ES, [M−H]−) m/z 255, 257, 259. 1HNMR (500 MHz, DMSO-d6): δ 10.63 (s, 1H), 8.15 (d, 1H, J=1.8 Hz), 7.95 (d, 1H, J=9.0 Hz), 7.77 (d, 1H, J=9 Hz), 7.68 (dd, 1H, J=9.0, 1.8 Hz), and 7.32 ppm (d, 1H, J=8.85 Hz). Elemental Analysis for C10H6BrClO: Calculated: C, 46.64; H, 2.35; N, 0.00. Found: C, 46.69; H, 2.35; N, 0.00.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. washThe organic phase was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was recrystallized in hot hexane
  7. washIt was rinsed with cold acetone
  8. customdried in vacuo at 60° C. for 30 minutes

Sources & evidence

ORD record
ord-b51546fdc1254e24b1891a3e8264effc
Source dataset
uspto-grants-2007_01
Patent number
US07163954B2

Reaction notes

Loading…