2-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 2-(1-Chloropropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 850874Notes

Reaction equation

[Cl:1][CH:2](Cl)[B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1.[CH2:13]([Mg]Br)[CH3:14]>O1CCCC1>[Cl:1][CH:2]([B:3]1[O:7][C:6]([CH3:9])([CH3:8])[C:5]([CH3:11])([CH3:10])[O:4]1)[CH2:13][CH3:14]

Participants

Conditions

Temperature: -78 °C

Procedure

2.64 g (12.5 mmol) of 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane were dissolved in 30 ml of tetrahydrofuran and the solution was cooled under a nitrogen atmosphere to -78° C. 11.8 ml (12.5 mmol) of 1.06M ethylmagnesium bromide were added dropwise and the solution was stirred at room temperature for 18 hours. The solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate and the organic layers were combined and dried over anhydrous sodium sulphate. After filtration and evaporation the oil obtained was distilled to give 2.04 g of 2-[1(RS)-chloropropyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; b.p. 53° C./0.8 mm Hg.

Workup

customThe solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution
extractionThe aqueous layer was extracted with ethyl acetate
dry with materialdried over anhydrous sodium sulphate
filtrationAfter filtration and evaporation the oil
customobtained
distillationwas distilled

Sources & evidence

ORD record: ord-9a62208003f141c781836d1ac6fe8da9
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06018020

Reaction notes

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