Trimethyl borate → (5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)boronic acid

HRID 2356611Notes

Reaction equation

HRID 2356611 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[F:17])=[C:4](I)[CH:3]=1.C([Mg]Cl)(C)C.[B:24](OC)([O:27]C)[O:25]C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[F:17])=[C:4]([B:24]([OH:27])[OH:25])[CH:3]=1

Participants

4

Reactant 3

HCID 8470Trimethyl borateHCID 247536874-Chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzeneHCID 178418918HCID 178418918, compound

Product 1

HCID 59384250(5-Chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}phenyl)boronic acid

Procedure

As for reaction 1, using 90.5 g 4-chloro-1-{[(4-chloro-2-fluorophenyl)methyl]oxy}-2-iodobenzene, 228 ml isopropylmagnesium chloride and 47.42 g trimethyl borate. Yield 66.8 g. NMR showed trace impurities. LCMS OK.

Workup

  1. customAs for reaction 1

Sources & evidence

ORD record
ord-e3563bca37ad47acbaf70ac970b4d027
Source dataset
uspto-grants-2010_07
Patent number
US07759369B2

Reaction notes

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