Iodine → 5-Bromonaphthalene-1,4-dicarboxylic acid

HRID 237119Notes

Reaction equation

HRID 237119 reaction equation
[C:1]1([C:14]([OH:16])=[O:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.II.[Br:24]Br>>[Br:24][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[C:4]([C:11]([OH:13])=[O:12])=[CH:3][CH:2]=[C:1]2[C:14]([OH:16])=[O:15]

Participants

5

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 24408BromineHCID 690651,4-Naphthalenedicarboxylic acid

Product 1

HCID 202858715-Bromonaphthalene-1,4-dicarboxylic acid

Procedure

44 parts of naphthalene-1,4-dicarboxylic acid are introduced in portions into 900 parts of concentrated sulphuric acid and the mixture is stirred to give a homogeneous suspension. A few crystals of iodine and 36 parts of bromine are then added and the whole is stirred overnight at room temperature. For working up, the mixture is discharged onto ice and filtered and the product is washed with water until neutral. 8-Bromo-naphthalene-1,4-dicarboxylic acid, which is thus obtained, can be purified by recrystallisation from glacial acetic acid. Melting point 288°-290°.

Workup

  1. customto give a homogeneous suspension
  2. stirringthe whole is stirred overnight at room temperature
  3. filtrationfiltered
  4. washthe product is washed with water until neutral

Sources & evidence

ORD record
ord-88dddcaaedf64f86bdb49e88fd42fea0
Source dataset
uspto-grants-1979_06
Patent number
US04159379

Reaction notes

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