N-Formylmorpholine → 6-Chloro-2,4-difluoro-3-trimethylsilylbenzaldehyde

HRID 1772868Notes

Reaction equation

[Li]CCCC.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([Si:14]([CH3:17])([CH3:16])[CH3:15])=[C:9]([F:18])[CH:8]=1.[CH:19](N1CCOCC1)=[O:20]>C1COCC1>[Cl:6][C:7]1[C:8]([CH:19]=[O:20])=[C:9]([F:18])[C:10]([Si:14]([CH3:15])([CH3:17])[CH3:16])=[C:11]([F:13])[CH:12]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 2.5M n-BuLi in hexanes (60 ml, 0.15 mol) was added drop-wise to a solution of (4-chloro-2,6-difluorophenyl)trimethylsilane (assumed 0.13 mol) in THF (180 mL) cooled to −70° C. under Ar. After the addition was complete, the mixture was stirred for 1 h before a solution of N-formylmorpholine (20 mL, 0.2 mol) in THF (25 mL) was added dropwise. The reaction was allowed to warm to rt with stirring and then cooled to 0° C. and quenched with H2O. Ether was added, the phases were separated, the aqueous phase was re-extracted with ether and the combined organics washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (35 g) as an orange oil which was used without further purification.

Workup

additionAfter the addition
additionwas added dropwise
temperatureto warm to rt
temperaturecooled to 0° C.
customquenched with H2O
additionEther was added
customthe phases were separated
extractionthe aqueous phase was re-extracted with ether
washthe combined organics washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8cd4521317aa40ea96bc54194ef87c60
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249160B2

Reaction notes

Loading…