Thionyl Chloride → 4-[(4-Chloromethylphenyl)sulfanyl]-2-methylphenoxy-acetic acid ethyl ester

HRID 985044Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2].S(Cl)([Cl:26])=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][Cl:26])=[CH:16][CH:15]=2)=[CH:9][C:8]=1[CH3:22])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

An oven-dried 1 L round-bottomed flask was charged with compound 7.2 (30.0 g, 90.2 mmol) and chloroform (300 mL) and the mixture was cooled to 0° C. Thionyl chloride (7.90 mL, 107 mmol) was added dropwise at 0° C., and the reaction was stirred at room temperature for 1 h. The reaction mixture was concentrated in vacuo to give 7.3 as a slightly yellow oil (33.5 g), which was used in the next step without further purification. 1H NMR (400 MHz) (CDCl3) δ 7.30-7.20 (4H, m); 7.12 (2H, d, J=8.3 Hz); 6.68 (1H, d, J=8.4 Hz); 4.65 (2H, s) ; 4.53 (2H, s); 4.27 (2H, q, J=7.1 Hz); 2.27 (3H, s); 1.30 (3H, t, J=7.1 Hz).

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-2a0691a34b64416da1515dc81efea72c
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06869975B2

Reaction notes

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