Thionyl Chloride → 1-(Benzyloxy)-4-(tert-butyl)-2-(chloromethyl)benzene

HRID 76777Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:10]=1[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:23]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][C:10]=1[CH2:11][Cl:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred solution of compound 4 (963 g, 3.56 mol) in anhydrous DCM (2000 mL) was added slowly SOCl2 (535 g, 4.5 mol) at 0° C. The mixture was stirred at 20° C. for 2 hours, then concentrated in vacuo to give compound 5 as an oil, which was used in the next reaction without further drying or purification.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-959544ec7cb143c48a8ef9cf375f0f66
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835639B2

Reaction notes

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