2-Chloro-6-fluoroanisole → HCID 178506719, compound

HRID 1404621Notes

Reaction equation

HRID 1404621 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B2OC(C)(C)C(C)(C)O2)=[C:4]([F:17])[C:3]=1[O:18][CH3:19].ClC1C=CC=C(F)C=1OC.C([Li:34])CCC>>[Cl:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([F:17])[C:5]([Li:34])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 27735812-Chloro-6-fluoroanisoleHCID 670174932-(4-Chloro-2-fluoro-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418339Butyllithium

Product 1

HCID 178506719HCID 178506719, compound

Procedure

Another embodiment of the present disclosure includes a method of forming 2-(4-chloro-2-fluro-3-methoxylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane that comprises contacting 2-chloro-6-fluoroanisole with n-butyl lithium to form 6-chloro-2-fluoro-3-lithioanisole. The 6-chloro-2-fluoro-3-lithioanisole may be contacted with trimethyl borate to form dimethyl 4-chloro-2-fluoro-3-methoxyphenylboronate. The dimethyl 4-chloro-2-fluoro-3-methoxyphenylboronate may be reacted with aqueous potassium hydroxide to form potassium (4-chloro-2-fluoro-3-methoxyphenyl)trihydroxyborate. The potassium (4-chloro-2-fluoro-3-methoxyphenyl)trihydroxyborate then may be reacted with aqueous hydrochloric acid to form 4-chloro-2-fluoro-3-methoxyphenylboronic acid. The 4-chloro-2-fluoro-3-methoxyphenylboronic acid may be reacted with 2,3-dimethyl-2,3-butanediol.

Sources & evidence

ORD record
ord-c7290afc70f743aaa14b66b33a066e8a
Source dataset
uspto-grants-2014_12
Patent number
US08912339B2

Reaction notes

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