Sodium hydride → HCID 21429131, compound

HRID 1403443Notes

Reaction equation

[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H][H].Br[CH2:17][CH:18]([O:22][CH2:23][CH3:24])[O:19][CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([O:19][CH:18]([O:22][CH2:23][CH3:24])[CH2:17][O:11][C:8]1[CH:7]=[CH:6][C:5]([C:4]([F:12])([F:13])[F:3])=[CH:10][CH:9]=1)[CH3:21]

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of sodium hydride (12.0 g, 500.00 mmol) in anhydrous DMF (500 mL) was added 4-(trifluoromethyl)phenol (35.0 g, 215.90 mmol) at 0° C. After hydrogen evolution had ceased, 2-bromo-1,1-diethoxyethane (55.0 g, 279.09 mmol) was added. The reaction was heated at 120° C. overnight. The mixture was poured into ice-water (2 L), extracted with ethyl acetate (3×150 mL), washed with 1N sodium hydroxide (3×100 mL) and brine (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to give the residue, which was purified by silica gel column chromatography eluting with 1% ethyl acetate in petroleum ether to afford 1-(2,2-diethoxyethoxy)-4-(trifluoromethyl)benzene as oil (8.0 g, 13%).

Workup

extractionextracted with ethyl acetate (3×150 mL)
washwashed with 1N sodium hydroxide (3×100 mL) and brine (3×100 mL)
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
customThe solvent was removed under vacuum
customto give the residue, which
customwas purified by silica gel column chromatography
washeluting with 1% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-978914db2fd44bc8ad6dd88f6c4051c5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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