Bis(2-bromoethyl) ether → 4-(3-Bromo-4-methoxyphenyl)-tetrahydro-2H-pyran-4-carbonitrile

HRID 1868651Notes

Reaction equation

CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:9]=[C:10]([CH2:16][C:17]#[N:18])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].Br[CH2:20][CH2:21][O:22][CH2:23][CH2:24]Br>CN1C(=O)CCC1.CCOCC>[Br:7][C:8]1[CH:9]=[C:10]([C:16]2([C:17]#[N:18])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of sodium tert-butoxide (6.7 g, 70 mmol) in 100 mL NMP stirred at 0° C. was treated dropwise with a mixture of 2-(3-bromo-4-methoxyphenyl)acetonitrile (6.3 g, 28 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.5 g, 28 mmol) in 30 mL ether. The mixture was allowed to warm to room temperature and was stirred for 3 hours, M+Na=318/320. The mixture was quenched with 100 mL H2O carefully and the pH was adjusted to 5. The mixture was extracted with ether (3×100 mL). The combined organic layers were washed with H2O (3×50 mL) and brine (20 mL). The organic layer was then dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% EtOAc/hexane to give 5.18 g of crude product as a yellow solid. MS m/e=318/320 (M+Na)+.

Workup

temperatureto warm to room temperature
stirringwas stirred for 3 hours
customThe mixture was quenched with 100 mL H2O carefully
extractionThe mixture was extracted with ether (3×100 mL)
washThe combined organic layers were washed with H2O (3×50 mL) and brine (20 mL)
dry with materialThe organic layer was then dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
custompurified by column chromatography
washeluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record: ord-6aa7f123782e48ffadd8b4eee9ab6933
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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