1,4-Dioxane → HCID 59166315, compound

HRID 2188945Notes

Reaction equation

[CH:1]1(P(C2CCCCC2)C2CCCCC2)[CH2:6]CCC[CH2:2]1.[C:20]([O-:23])(=O)[CH3:21].[K+].[O:25]1CCO[BH:26]1.Br[C:31]1[CH:36]=[CH:35][C:34]([C:37]([OH:46])([C:42]([F:45])([F:44])[F:43])[C:38]([F:41])([F:40])[F:39])=[CH:33][CH:32]=1.O1CCOC[CH2:48]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[F:39][C:38]([F:41])([F:40])[C:37]([C:34]1[CH:35]=[CH:36][C:31]([B:26]2[O:25][C:1]([CH3:6])([CH3:2])[C:20]([CH3:21])([CH3:48])[O:23]2)=[CH:32][CH:33]=1)([OH:46])[C:42]([F:45])([F:44])[F:43]

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of Pd(dba)2 (100 mg, 0.20 mmol) and PCy3 (130 mg, 0.50 mmol) in dioxane (8 mL) were added potassium acetate (920 mg, 9.4 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane (1.8 g, 7.1 mmol) and 2-(4-bromophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (2.0 g, 6.2 mmol). The mixture was heated at 80° C. overnight. The mixture was quenched with H2O and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography (0-5% ethyl acetate-petroleum ether) to afford 1,1,1,3,3,3-hexafluoro-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ol (870 mg, 38%). 1H NMR (CDCl3, 400 MHz) δ 7.89 (d, J=8.0 Hz, 2H), 7.71 (d, J=8.0 Hz, 2H), 3.50 (s, 1H), 1.35 (s, 12H).

Workup

customThe mixture was quenched with H2O
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (0-5% ethyl acetate-petroleum ether)

Sources & evidence

ORD record: ord-6deb75d61594470c96b8603397fe52aa
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324207B2

Reaction notes

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