Thionyl Chloride → 4-(Chloromethyl)-2-(1,1-dimethylethyl)-3'-(methyloxy)-1,1'-biphenyl

HRID 1662332Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A dry, round bottom flask containing 12.2 (0.82 g, 3.04 mmol) and DCM (8.5 mL) was cooled to 0° C. After 15 minutes, thionyl chloride (1.50 mL, 20.56 mmol) was carefully added dropwise at 0° C. Upon complete addition of thionyl chloride, the mixture was allowed to warm to room temperature and stirred overnight. After 25 hours, the reaction was concentrated under reduced pressure. The residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes). Fractions containing the desired product were combined and concentrated to provide 12.3 as a colorless oil (0.82, 93%). 1H NMR (500 MHz, CDCl3) δ ppm 7.53 (1H, d, J=1.7 Hz), 7.28 (3H, m), 7.03 (1H, d, J=7.8 Hz), 6.90 (3H, m), 4.65 (2H, s), 3.82 (3H, s), 1.23 (9H, s).

Workup

temperatureto warm to room temperature
waitAfter 25 hours
concentrationthe reaction was concentrated under reduced pressure
customThe residue was then purified by flash chromatography (SiO2 gel 60, eluted with 0%-15% EtOAc in hexanes)
additionFractions containing the desired product
concentrationconcentrated

Sources & evidence

ORD record: ord-11d38465f9414924ac655379dc63a1d2
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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