HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Boron tribromide → 4-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

HRID 1798100
Notes
Print preview

Reaction equation

HRID 1798100 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[O:17]C)=[O:7].B(Br)(Br)Br>ClCCl>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([O:15][CH3:16])=[CH:10][C:9]=1[OH:17])=[O:7].[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]=1[OH:17])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 582925834-(2,4-Dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester

Product 2

HCID 582926554-(2,4-Dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl esterYield 34%HCID 582928314-(2-Hydroxy-4-methoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 4-(2,4-dimethoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (1.0 g, 3.76 mmol) in dichloromethane (10 mL) was added 1 M BBr3 in dichloromethane (15.04 mL). The reaction mixture was stirred at room temperature for 48 hours then poured onto ice and extracted with EtOAc. The organic extracts were dried and concentrated in vacuo. The residue was dissolved in concentrated H2SO4 (0.2 mL) and MeOH (10 mL) and the mixture was heated at 75° C. for 1 hour. The mixture was concentrated in vacuo and the residue was purified by silica gel flash column chromatography to give 4-(2-hydroxy-4-methoxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (0.300 g, 31%) and 4-(2,4-dihydroxy-6-methyl-phenyl)-4-oxo-butyric acid methyl ester (0.300 g, 34%).

Workup

  1. additionthen poured onto ice
  2. extractionextracted with EtOAc
  3. customThe organic extracts were dried
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in concentrated H2SO4 (0.2 mL)
  6. temperatureMeOH (10 mL) and the mixture was heated at 75° C. for 1 hour
  7. concentrationThe mixture was concentrated in vacuo
  8. customthe residue was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-c072c1aa52c5411d8b0da9af936fa858
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343944B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes