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

HRID 2285494Notes

Reaction equation

HRID 2285494 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-e4ba96f305fd44bbb6b5e0c2eea5b6f8
Source dataset
uspto-grants-1982_04
Patent number
US04323503

Reaction notes

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