Water → Bis(pentafluorophenyl)borinic acid

HRID 1359538

Reaction equation

[F:1][C:2]1[C:7]([B:8](C2C(F)=C(F)C(F)=C(F)C=2F)[C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=2[F:19])=[C:6]([F:31])[C:5]([F:32])=[C:4]([F:33])[C:3]=1[F:34].[OH2:35]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([B:8]([C:9]2[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=2[F:19])[OH:35])=[C:6]([F:31])[C:5]([F:32])=[C:4]([F:33])[C:3]=1[F:34]

Participants

Conditions

Temperature: 100 °C

Procedure

20 g (39 mmol) of tris(pentafluorophenyl)borane together with 150 ml of toluene are placed in a reaction vessel and the mixture is subsequently heated 100° C. 1.8 ml (97.5 mmol) of water in 40 ml of toluene are subsequently added dropwise to this solution over a period of 30 minutes. The mixture is subsequently stirred for another two hours at 100° C. After this time, the solvent is taken off in an oil pump vacuum. The residue does not have to be purified further. This gives 12.6 g (89%) of colorless bis(pentafluorophenyl)hydroxyborane. The boroxin content is 5%. 1H-NMR(C6D6, 400 MHz): −133.1 (m, 4 F, o-B(C6F5)2), −147.9 (m, 2 F, p-B(C6F5)2), −161.1 (m, 4 F, m-B(C6F5)2) ppm.

Workup

customis subsequently heated 100° C
customto be purified further

Sources & evidence

ORD record: ord-84dec26e82cf41c48223f995df9879a4
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06600066B1

Linked notes

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