Bis(2-bromoethyl) ether → 4-(3-Methoxyphenyl)oxane-4-carbonitrile

HRID 1868668

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]#[N:13])[CH:8]=[CH:9][CH:10]=1.Br[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Br>CN1C(=O)CCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2([C:12]#[N:13])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of NaH (3.2 g, 79 mmol) in 50 mL NMP stirred at 0° C., was treated dropwise with a mixture of 2-(3-methoxyphenyl)acetonitrile (3.9 g, 26 mmol) and 1-bromo-2-(2-bromoethoxy)ethane (6.1 g, 26 mmol) in 20 mL. The mixture was allowed to warm to room temperature and stirred for 15 hours, M+1=218. The mixture was then carefully quenched with 100 mL H2O 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 dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 10-20% EtOAc/hexane to give 5.28 g of the crude product 5.28 g as a pale yellow oil. MS (m/z)=218 (M+H)+.

Workup

temperatureto warm to room temperature
stirringstirred for 15 hours
customThe mixture was then carefully quenched with 100 mL H2O
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 dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
custompurified by column chromatography
washeluting with 10-20% EtOAc/hexane

Sources & evidence

ORD record: ord-b3c61d16b4bf41a7a9fc7033fef635f9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Linked notes

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