Hydrochloric Acid → B-[2,3-Difluoro-4′-(octyloxy)[1,1′-biphenyl]-4-yl]boronic acid

HRID 36819

Reaction equation

[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=2[F:23])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.C([O:32][B:33](OC(C)C)[O:34]C(C)C)(C)C.Cl>C1COCC1>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([B:33]([OH:34])[OH:32])=[C:18]([F:22])[C:17]=2[F:23])=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: -70 °C

Procedure

After 2.72 g of the 4-n-octyloxy-2', 3'-difluorobiphenyl was dissolved in 20 ml of a dried THF, the solution thus formed was cooled down to -70° C. under a nitrogen atmosphere and added dropwise with 5.5 ml of butyllithium (1.6 mol/liter hexane solution). The solution was continuously stirred at the same temperature for 2 hours, and then added dropwise with a THF solution containing 3.21 g of triisopropylborate. After the solution was stirred at an ambient temperature for 12 hours, it was added with 7.7 ml of a 10% aqueous hydrochloric acid solution and further stirred for 1 hour. Then, the same after-treatments as in [1] in Example 1 were repeated to obtain 2.27 g of 4-(p-n-octyloxyphenyl)-2,3-difluorobenzene boronic acid.

Workup

customthe solution thus formed
stirringAfter the solution was stirred at an ambient temperature for 12 hours
stirringfurther stirred for 1 hour

Sources & evidence

ORD record: ord-4dd5a74a02604455bb79697d682effd8
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05417885

Linked notes

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