Boronic Acid → 3-Octyloxy-6-pyridazineboronic acid

HRID 1721580Notes

Reaction equation

[CH2:1]([O:9][C:10]1[N:11]=[N:12][C:13](Cl)=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([Li])CCC.[BH:22]([OH:24])[OH:23]>C1COCC1.CCCCCC.C(OCC)C.[Cl-].[Cl-].[Zn+2]>[CH2:1]([O:9][C:10]1[N:11]=[N:12][C:13]([B:22]([OH:24])[OH:23])=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

Conditions

Temperature: -78 °C

Procedure

17.1 g (70.6 mmol) of 3-octyloxy-6-chloropyridazine are dissolved in 100 ml of absolute THF and cooled to -78° C. under a protective gas. 47.1 ml (75.2 mmol) of 1.6 molar n-butyllithium solution in hexane are then added dropwise over the course of 30 minutes. The mixture is stirred at -78° C. for a further 30 minutes. 216 ml (215.7 mmol) of 1.0 molar ZnCl2 solution in diethyl ether are subsequently slowly added dropwise, during which the temperature must not exceed -60° C. When the addition is complete, the mixture is stirred for a further 30 minutes. The crude boronic acid is employed directly, without isolation from the solution, for the subsequent couplings.

Workup

customexceed -60° C
additionWhen the addition
stirringthe mixture is stirred for a further 30 minutes

Sources & evidence

ORD record: ord-000217ba6f514ea88439ed3a0ee8e135
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05512207

Reaction notes

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