Water → 6-bromo-1H,3H-naphtho[1,8-cd]thiopyran

HRID 2056740Notes

Reaction equation

HRID 2056740 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[C:7]([CH2:12]Br)[CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:14]Br)=[CH:4][CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[S:28]([O-])([O-])(=O)=O.[Na+].[Na+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][S:28][CH2:12][C:7]3[C:6]=2[C:11]=1[CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 962Water2×HCID 24436Sodium SulfateHCID 73972Sodium sulfide nonahydrateHCID 693065361-Bromo-4,5-bis(bromomethyl)naphthalene

Product 1

HCID 693077926-bromo-1H,3H-naphtho[1,8-cd]thiopyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-bromo-4,5-bis(bromomethyl)-naphthalene (0.38 g, 0.97 mmol) and sodium sulfide nonahydrate (0.25 g, 1.04 mmol) in dimethylformamide (13 mL) was stirred at room temperature for 5 h, in the presence of sodium sulfate as scavenger for the water. The reaction mixture was poured into water and extracted into diethyl ether. The combined organic extracts were washed with water, dried (Na2SO4) and concentrated to dryness, to yield 6-bromo-1H,3H-naphtho[1,8-cd]thiopyran as a pale yellow solid.

Workup

  1. extractionextracted into diethyl ether
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-59625392f15742afada030f544b6b585
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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