Tyrosol → 2-(4-((5-Chloro-6-(trifluoromethyl)pyridin-2-yl)oxy)phenyl)ethanol

HRID 705913Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([Cl:12])=[CH:4][CH:3]=1.[OH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:12][C:5]1[CH:4]=[CH:3][C:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][OH:13])=[CH:17][CH:18]=2)=[N:7][C:6]=1[C:8]([F:11])([F:10])[F:9]

Participants

Conditions

Temperature: 110 °C

Procedure

To the solution of 6-bromo-3-chloro-2-(trifluoromethyl)pyridine (2 g, 7.68 mmol) and 4-(2-hydroxyethyl)phenol (1.061 g, 7.68 mmol) in DMF (30 mL) was added K2CO3 (1.592 g, 11.52 mmol). The mixture was heated at 110° C. for 2 h. Purification via reverse phase flash chromatography afforded the title compound (200 mg, 8.2% yield) as brown solid. LCMS: rt=3.14 min, [M+H+]=318

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-9f5d4421ebb2456c976280a847c92a71
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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