3,5-Dibromosalicylaldehyde → HCID 86702313, compound

HRID 923820Notes

Reaction equation

HRID 923820 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=O.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21](O)=[O:22])=[CH:16][CH:15]=1.C(N(CC)CC)C.[OH-].[Na+]>C(OC(=O)C)(=O)C>[Br:10][C:8]1[CH:7]=[C:4]2[C:3](=[C:2]([Br:1])[CH:9]=1)[O:11][C:21](=[O:22])[C:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)=[CH:5]2

Participants

6

Reactant 4

HCID 70243,5-DibromosalicylaldehydeHCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 14798Sodium Hydroxide

Product 1

HCID 86702313HCID 86702313, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
80 °C

Procedure

3,5-Dibromo-2-hydroxybenzaldehyde (30.0 g, 107 mmol) [CAS-Nr. 90-59-5] and 4-methoxyphenylacetic acid (35.7 g, 166 mmol) are heated in 51 ml acetic anhydride and 60 ml triethylamine overnight at reflux. The reaction mixture is cooled down to 80° C. and poured onto 1000 ml 2 M sodium hydroxide under stirring. After 5 min the precipitated product is filtered by vacuum, washed with water and digested two times with 100 ml ethanol. 6,8-Dibromo-3-(4-methoxy-phenyl)-chromen-2-one is obtained as a yellow solid.

Workup

  1. filtrationAfter 5 min the precipitated product is filtered by vacuum
  2. washwashed with water

Sources & evidence

ORD record
ord-aa8d16da34e843579711fdc811f1f0e9
Source dataset
uspto-grants-2016_03
Patent number
US09279082B2

Reaction notes

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