Water → HCID 21191969, compound

HRID 1457436Notes

Reaction equation

HRID 1457436 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:15]([OH:17])=[O:16])[CH:8]=2)[CH:3]=1.[Br:18]Br.O>C(Cl)(Cl)Cl.CS(C)=O>[Br:18][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:15]([OH:17])=[O:16])=[CH:6][CH:5]=2)[CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:2]=1[OH:1]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 98160552-hydroxynaphthalen-3,6-dicarboxylic acid

Product 1

HCID 21191969HCID 21191969, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent2×

Procedure

2-Hydroxy-3,6-di-hydroxycarbonylnaphthalene (11.8 g) was dissolved in chloroform (300 g) and dimethyl sulfoxide (100 g), followed by ice-cooling. Then, a solution of bromine (8.0 g) and chloroform (50 g) was added dropwise at not more than 5° C. over 2 hours. After continuously stirring for 1 hour, this solution was poured into water (1500 g) dropwise. The deposit was filtered and then washed with water and dispersed in a small amount of methanol. The dispersion was concentrated under reduced pressure at room temperature and then dried under vacuum to obtain 15.1 g of 1-bromo-2-hydroxy-3,6-di-hydroxycarbonylnaphthalene as a whitish brown crystal (DSC analysis value: 145.2° C.).

Workup

  1. temperaturecooling
  2. filtrationThe deposit was filtered
  3. washwashed with water
  4. additiondispersed in a small amount of methanol
  5. concentrationThe dispersion was concentrated under reduced pressure at room temperature
  6. customdried under vacuum

Sources & evidence

ORD record
ord-79450f3ca4774e2f97b7aa0c80aec4ad
Source dataset
uspto-grants-1998_12
Patent number
US05847233

Reaction notes

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