Thionyl Chloride → 4-(Chloromethyl)-2-fluoro-1-methylbenzene

반응식

S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[C:8]([CH2:13]O)[CH:9]=[CH:10][C:11]=1[CH3:12]>>[Cl:3][CH2:13][C:8]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:6]([F:5])[CH:7]=1

참가 물질

반응물 2

HCID 24386Thionyl Chloride

HCID 2774590(3-Fluoro-4-methylphenyl)methanol

생성물 1

HCID 186241474-(Chloromethyl)-2-fluoro-1-methylbenzene

실험 절차

Thionyl chloride (0.892 g, 7.5 mmol) was added to a solution of the product of STEP 1 (1.0 g, 6.4 mmol) dropwise at 0° C. After 30 min, the reaction was quenched with crushed ice carefully, and diluted with H2O. The product was extracted with ether. The organic layer washed with saturated NaHCO3, brine and dried with Na0.2SO4. Ether was evaporated and the residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9) to give a clear liquid in 10.5 g. NMR spectra of the product were consistent for the proposed structure.

후처리

customthe reaction was quenched with crushed ice carefully
additiondiluted with H2O
extractionThe product was extracted with ether
washThe organic layer washed with saturated NaHCO3, brine
customdried with Na0.2SO4
customEther was evaporated
customthe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/9)
customto give a clear liquid in 10.5 g

출처 및 근거

ORD 기록: ord-8c5ecd99956f45fcb884e9c31c6a50b6
출처 데이터셋: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US06531494B1

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