Tetrahydrofuran → 4-Methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid

HRID 1666448Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:19])=[C:6]([CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.C1COCC1.[Li]CCCC>C1(C)C=CC=CC=1>[CH3:19][C:5]1[CH:4]=[CH:3][C:2]([B:24]([OH:25])[OH:23])=[CH:18][C:6]=1[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1

Participants

Conditions

Temperature: -40 °C

Procedure

2-(5-Bromo-2-methylphenoxy)-5-(trifluoromethyl)pyridine (1 g, 0.003 mol) and triisopropylborate (0.8 mL, 0.003 mol) were dissolved in toluene (20 mL) and THF (5 mL) and cooled to −78° C. under a N2 atmosphere. n-BuLi (2.69 mL, 0.003 mol) was added while maintaining the reaction at −70° C. and then the reaction was stirred for 1 h at −40° C. Gradually the temperature was increased to −20-0° C. and then the reaction was quenched with 2N HCl. The reaction mixture was warmed to RT, concentrated and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (1.13 g). m/z (296.4, 298.3, M− H−).

Workup

temperaturewhile maintaining
customthe reaction at −70° C.
temperatureGradually the temperature was increased to −20-0° C.
customthe reaction was quenched with 2N HCl
temperatureThe reaction mixture was warmed to RT
concentrationconcentrated
extractionextracted with EtOAc
extractionThe organic extract
dry with materialwas dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-9f89c33ac5314d4da249f73f88423840
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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