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

HRID 2170944Notes

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-d005ac4e7bf548bc8a15c6d08e9f513d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051316B2

Reaction notes

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