Thionyl Chloride → 6,7-Dibromo-8-nitro-1,4-benzodioxane-5-carbonyl chloride

HRID 1660024Notes

Reaction equation

HRID 1660024 reaction equation
[Br:1][C:2]1[C:11]([Br:12])=[C:10]([N+:13]([O-:15])=[O:14])[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[C:16]([OH:18])=O.S(Cl)([Cl:21])=O>>[Br:1][C:2]1[C:11]([Br:12])=[C:10]([N+:13]([O-:15])=[O:14])[C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[C:16]([Cl:21])=[O:18]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 205447596,7-Dibromo-8-nitro-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Product 1

HCID 205447556,7-Dibromo-8-nitro-1,4-benzodioxane-5-carbonyl chlorideYield 91%

Procedure

96 g of 6,7-dibromo-8-nitro-1,4-benzodioxane-5-carboxylic acid and 200 ml of thionyl chloride were introduced into a balloon flask provided with an agitator and a thermometer. The mixture was heated under reflux and then the excess thionyl chloride was removed under vacuum. The residue was dissolved in 100 ml of isopropyl ether and then the solvent removed and the product air-dried. 91 g of 6,7-dibromo-8-nitro-1,4-benzodioxane-5-carbonyl chloride were obtained (M.P.: 215° C.; yield: 91%).

Workup

  1. customprovided with an agitator
  2. temperatureThe mixture was heated
  3. temperatureunder reflux
  4. customthe excess thionyl chloride was removed under vacuum
  5. dissolutionThe residue was dissolved in 100 ml of isopropyl ether
  6. customthe solvent removed
  7. customthe product air-dried

Sources & evidence

ORD record
ord-e49f903ead5e436f9a73e06cbee9ba4a
Source dataset
uspto-grants-1981_12
Patent number
US04306072

Reaction notes

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