Toluene → HCID 66611961, compound

HRID 2204701Notes

Reaction equation

HRID 2204701 reaction equation
Br[C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[F:15][C:16]([F:21])([F:20])C([O-])=O.[K+].C1(C)C=CC=CC=1>CN(C)C=O.[Cu]I>[CH3:14][C:3]1[C:2]([C:16]([F:21])([F:20])[F:15])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([O:12][CH3:13])[CH:4]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 21043961Methyl 5-bromo-2-methoxy-4-methylbenzoateHCID 23662811Potassium trifluoroacetate

Product 1

HCID 66611961HCID 66611961, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of methyl 5-bromo-4-methyl-2-(methyloxy)benzoate (may be prepared as described in Description 43; 2.5 g, 9.65 mmol) in N,N-dimethylformamide (40 ml) was added copper (I) iodide (4.04 g, 21.23 mmol) and potassium trifluoroacetate (2.94 g, 19.30 mmol). Toluene (10 ml) was added and the mixture heated in Dean Stark apparatus at 170° C. for 45 minutes. The toluene was removed via the Dean Stark trap and the resulting mixture was heated for 18 hours at 170° C. The mixture was diluted with water (10 ml) and ethyl acetate (20 ml) and the solid was removed using Celite. The filtrate was taken and the organic layer separated, dried (MgSO4) and the solvent removed in vacuo. The residue was purified by column chromatography (SiO2, 50% Cyclohexane/diethyl ether) to yield the title compound as a white solid. 1.76 g.

Workup

  1. customThe toluene was removed via the Dean Stark trap
  2. temperaturethe resulting mixture was heated for 18 hours at 170° C
  3. additionThe mixture was diluted with water (10 ml) and ethyl acetate (20 ml)
  4. customthe solid was removed
  5. customthe organic layer separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by column chromatography (SiO2, 50% Cyclohexane/diethyl ether)

Sources & evidence

ORD record
ord-61aa5484447c4573ade7f59dba9cb7a2
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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