Methyl formate → Ethyl 4-tert-butyl-5-chloro-2-ethoxybenzoate

HRID 2425588Notes

Reaction equation

[C:1]([C:5]1[C:10]([Cl:11])=[CH:9][C:8](I)=[C:7]([O:13][CH2:14][CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][O-].[Na+].[CH3:19][O:20][CH:21]=[O:22]>O1CCOCC1>[C:1]([C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:21]([O:20][CH2:19][CH3:16])=[O:22])=[C:7]([O:13][CH2:14][CH3:15])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a degassed solution of 4-tert-butyl-5-chloro-2-ethoxy-1-iodobenzene (2.2 g, 6.4 mmol), sodium methoxide (0.52 g, 9.6 mmol) and dichlorobistriphenylphosphinepalladium (0.25 g, 0.4 mmol) in dioxane (20 mL) was added methylformate (1.2 mL, 19.4 mmol). The resulting mixture was heated in an oil bath (60° C.) for 18 h and then allowed to cool. The solution was diluted with dioxane and filtered through a plug of Celite and concentrated. Purification of the crude residue by flash chromatography over silica gel using 5-20% ethyl acetate in hexanes gave ethyl 4-tert-butyl-5-chloro-2-ethoxybenzoate (1.39 g, 80%) as a clear oil.

Workup

temperatureto cool
filtrationfiltered through a plug of Celite
concentrationconcentrated
customPurification of the crude residue by flash chromatography over silica gel using 5-20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-7f24652838d440f38232ada8f530c928
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964724B2

Reaction notes

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