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

HRID 850874
Notes
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Reaction equation

HRID 850874 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 110420412-(Dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418443HCID 178418443, compound

Product 1

HCID 193646402-(1-Chloropropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneYield 79.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. customThe solution was partitioned between ethyl acetate, saturated sodium chloride solution and 2M hydrochloric acid solution
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationAfter filtration and evaporation the oil
  5. customobtained
  6. 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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