Bromine → HCID 19756153, compound

HRID 1587725Notes

Reaction equation

HRID 1587725 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:5]=[C:6]([C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:11]=1[OH:12])[CH:7]=[O:8]>C(O)(=O)C.O>[Br:1][C:10]1[C:9]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]([CH:5]=[C:4]([OH:3])[C:11]=1[OH:12])[CH:7]=[O:8]

Participants

5

Reactant 2

HCID 24408BromineHCID 19756154HCID 19756154, compound

Product 1

HCID 19756153HCID 19756153, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Bromine (192 μl) was added to a suspension of 3,4-dihydroxy-6-(methoxycarbonylmethyl)benzaldehyde (0.79 g) in acetic acid (15 ml). The reaction mixture was stirred at ambient temperature for 5-6 hours, diluted with water (30 ml) and extracted into ethyl acetate (200 ml). The organic phase was washed with NaHCO3, water (100 ml) and brine, dried and evaporated under reduced pressure to give a brown solid. This was purified by chromatography using aqueous acetonitrile mixtures to give 3-bromo-4,5-dihydroxy-2-(methoxycarbonylmethyl)benzaldehyde (300 mg); NMR (DMSO-d6) 3.61(s,3H); 4.24(s,2H); 7.24(s,1H); 9.8(s,1H): CI M/S (M+H)+ 291.

Workup

  1. extractionextracted into ethyl acetate (200 ml)
  2. washThe organic phase was washed with NaHCO3, water (100 ml) and brine
  3. customdried
  4. customevaporated under reduced pressure
  5. customto give a brown solid
  6. customThis was purified by chromatography

Sources & evidence

ORD record
ord-b869da637b7f4b94812826d44ddfd8db
Source dataset
uspto-grants-1993_06
Patent number
US05219848

Reaction notes

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