4-Chlorophenylboronic acid → HCID 15191520, compound

HRID 1500208Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(O[I:15](OC(=O)C)[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=1[CH3:24])(=O)C.[F:29][B-:30]([F:33])([F:32])[F:31].C1([I+]C2C=CC=CC=2)C=CC=CC=1.F[B-](F)(F)F.[Na+]>C(Cl)Cl>[F:29][B-:30]([F:33])([F:32])[F:31].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I+:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Chlorophenylboronic acid (3.0 g, 8.2 mmol), methylene chloride (82 ml) and boron trifluoride ethyl ether complex (1.29 g, 9.1 mmol) were charged and cooled to 0° C. A solution of diacetoxy(2,4,6-trimethylphenyl)iodine (III) (3.0 g, 8.2 mmol) synthesized in (i) in methylene chloride (82 ml) was added dropwise, and the reaction was carried out at 0° C. for 1.5 hours. A saturated aqueous solution of sodium fluoroborate (18.1 g, 164.8 mmol) was added dropwise, and the mixture was extracted with addition of water and methylene chloride. The organic layer was dried with anhydrous sodium sulfate, concentrated to dryness under reduced pressure, and purified by recrystallization to give the title compound (3.36 g, 93.5%).

Workup

additionwas added dropwise
extractionthe mixture was extracted with addition of water and methylene chloride
dry with materialThe organic layer was dried with anhydrous sodium sulfate
concentrationconcentrated to dryness under reduced pressure
custompurified by recrystallization

Sources & evidence

ORD record: ord-a2e25adc78164c389eab0b6de33af9ce
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206129B2

Reaction notes

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