Diethyl Ether → 2-(3-Bromopropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

HRID 512206Notes

Reaction equation

HRID 512206 reaction equation
O[CH2:2][CH2:3][CH2:4][O:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[C:7]#[N:8].C(Br)(Br)(Br)[Br:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC>C(Cl)Cl>[Br:17][CH2:2][CH2:3][CH2:4][O:5][CH:6]([C:9]1[CH:10]=[N:11][C:12]([CH3:15])=[N:13][CH:14]=1)[C:7]#[N:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 867162352-(3-Hydroxypropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

Product 1

HCID 867162362-(3-Bromopropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3-hydroxypropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile (54 mg, 0.26 mmol) and CBr4 (259 mg, 0.782 mmol) in DCM (3 ml) was cooled at 0° C. Triphenylphosphine (205 mg, 0.782 mmol) in DCM (1 ml) was added dropwise over a period of 5 minutes. The reaction was stirred for 2 hours and then allowed to warm to room temperature. To the mixture was added Et2O (5 mL) and the cloudy solution was filtred through a plug of celite. The resulting solution was concentrated in vacuo and purified by flash chromatography to yield 2-(3-Bromopropoxy)-2-(2-methylpyrimidin-5-yl)acetonitrile.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-90d143287a9847ae8b6caa84e5d782a4
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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