2,2-Dimethyl-1,3-dioxane-4,6-dione → 8-Bromo-2-oxo-2H-chromene-3-carboxylic acid

HRID 240025Notes

Reaction equation

HRID 240025 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.CC1(C)O[C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1>O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]2[C:3]=1[O:10][C:17](=[O:18])[C:16]([C:14]([OH:15])=[O:13])=[CH:5]2

Participants

4

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 497566818-Bromo-2-oxo-2H-chromene-3-carboxylic acidYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

3-bromohydroxybenzaldehyde (139.5 mg, 0.69 mmol) and Meldrum's acid (100 mg, 0.69 mmol) were combined in H2O (1 mL). The solution was stirred at 75° C. for 2 h. After cooling to room temperature, the precipitate was filtered and dried at suction to give 135.0 mg of 8-bromo-3-carboxy-coumarin in an 73% yield.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe precipitate was filtered
  3. customdried at suction

Sources & evidence

ORD record
ord-76c449a9ec444e4a9bccaeb54c2e4f8c
Source dataset
uspto-grants-2014_02
Patent number
US08642788B2

Reaction notes

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