Isopropanol → 4-Bromo-2-(trifluoromethoxy)benzaldehyde

HRID 2090186Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1.C([Li])CCC.[CH:19](N1CCOCC1)=[O:20].C(O)(C)C>C1COCC1.CCCCCC.ClCCl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:19]=[O:20])=[C:4]([O:9][C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

20.00 g (54.51 mmol) of 4-bromo-2-(trifluoromethoxy)iodobenzene are dissolved in 200 ml of THF and cooled to −78° C. Then 26.16 ml (65.41 mmol) of a 2.5 M solution of n-butyllithium in hexane are added dropwise. The mixture is stirred for 30 min and then 14.43 g (125.37 mmol) of N-formylmorpholine are metered in. After complete conversion is detected (TLC check), solvolysis is carried out at −78° C. with isopropanol. Warming to room temperature is followed by addition of water and extraction twice with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution and dried with sodium sulfate, and the solvent is distilled out under reduced pressure. The residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1). 11.43 g (78% of theory) of the title compound are obtained.

Workup

temperatureWarming to room temperature
washThe combined organic phases are washed with saturated sodium chloride solution
dry with materialdried with sodium sulfate
distillationthe solvent is distilled out under reduced pressure
customThe residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 5:1)

Sources & evidence

ORD record: ord-57bab9a1a28240a58c40263cc6c2637e
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436180B2

Reaction notes

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