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

HRID 1359230Notes

Reaction equation

HRID 1359230 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-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of 6-bromo-2-naphthol (10.0 g, 0.045 mol) in chloroform (100 mL) was added sulfuryl chloride (6.4 mL, 0.09 mol). The mixture was stirred at reflux for 0.5 hour then at room temperature for 2 hours. Water (50 mL) was added and the organic phase was washed with water then solvent evaporated. The solid was crystallized from hexane and air dried to give the title compound as a solid, mp 103-105° C. Mass spectrum (−ES, [M−H]−) m/z 255, 257, 259. 1HNMR (500 MHz, DMSO-d6): δ10.63 (s, 1H), 8.15 (d, 1H, J=1.8 Hz), 7.95 (d, 1H, J=9.0 Hz), 7.7 (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. temperatureat reflux for 0.5 hour
  2. washthe organic phase was washed with water
  3. customsolvent evaporated
  4. customThe solid was crystallized from hexane and air
  5. customdried

Sources & evidence

ORD record
ord-fd415d9415cd422c812bfe7a30042813
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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