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Potassium Carbonate → 3-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

HRID 1728178
Notes
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Reaction equation

HRID 1728178 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15][O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

Product 1

HCID 575659193-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl esterYield 904.3%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

5-Bromo-2-hydroxy-benzaldehyde (4 g, 2 mmol), 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (5.46 g, 24 mmol), K2CO3 (5.5 g, 40 mmol) and KI (0.1 g) were mixed in DMF (20 mL). Then the mixture was irradiated under microwave at 150° C. for 1 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was separated, dried over Na2SO4 and concentrated to give title compound 5.7 g.

Workup

  1. customThen the mixture was irradiated under microwave at 150° C. for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N NaOH
  6. customThen the organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-433e15e370e94c9392ad3d4f37f5b16b
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07495007B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes