1-(Bromomethyl)-2,3-dichlorobenzene → 2-(2,3-Dichlorobenzyl)-3-oxobutanenitrile

HRID 510417Notes

Reaction equation

[C:1]([CH:3]([Na])[C:4](=[O:6])[CH3:5])#[N:2].Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:11]=1[Cl:17]>CN(C=O)C.[Cl-].[NH4+]>[Cl:17][C:11]1[C:12]([Cl:16])=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][CH:3]([C:4](=[O:6])[CH3:5])[C:1]#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1-cyano-2-oxopropyl)sodium (1.28 g, 12.16 mmol) in DMF (80 mL) was added 1-(bromomethyl)-2,3-dichlorobenzene (2.043 g, 8.51 mmol) dropwise over a period of 30 min at 0° C. The mixture was stirred at 0° C. for 1 h and at room temperature for 2 h. Then this solution was diluted with saturated aq. ammonium chloride solution. The resulting solution was extracted with ethyl acetate (80 mL×3). The combined organic layers were washed with water and brine, dried over sodium sulphate, concentrated under reduced pressure to give the crude product (2.19 g, 100%), which was used for the next step without further purification. LC/MS: MS (ES+) m/e 242 (MH+).

Workup

extractionThe resulting solution was extracted with ethyl acetate (80 mL×3)
washThe combined organic layers were washed with water and brine
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ac37c6ea0f094817a14a9b14e3919a7e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096605B2

Reaction notes

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