Bis(2-bromoethyl) ether → HCID 86716215, compound

HRID 512187Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][N:3]=1.Br[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Br.CC([O-])(C)C.[K+]>O1CCOCC1>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-(2-methylpyrimidin-5-yl)acetonitrile (4 g, 0.03 amol) and 1-bromo-2-(2-bromoethoxy)ethane (7.66 g, 0.033 mol) in 1,4-dioxane (60 mL) was added t-BuOK (66 mL, 0.066 mol, 1M in THF) and heated to 80° C. for 4 h. The reaction mixture was cooled to room temperature, quenched by sat.NH4Cl. The 1,4-dioxane was removed under reduced pressure. The residue aqueous layer was extracted with EtOAc (3×150 mL). The organic layer was dried over Na2SO4 and concentracted to give 4-(2-methylpyrimidin-5-yl)tetrahydro-2H-pyran-4-carbonitrile (5.5 g, yield: 90.5%). 1H NMR (CDCl3 400 MHz): δ8.75 (s, 2H), 4.15-4.05 (m, 2H), 3.95-3.85 (m, 2H), 2.75 (s, 3H), 2.15-2.00 (m, 4H).

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched
customThe 1,4-dioxane was removed under reduced pressure
extractionThe residue aqueous layer was extracted with EtOAc (3×150 mL)
dry with materialThe organic layer was dried over Na2SO4

Sources & evidence

ORD record: ord-50b993b6ebfb4b48b92fb0b8d87e3751
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102591B2

Reaction notes

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