1,4-Dibromobutane → HCID 21896328, compound

HRID 719067Notes

Reaction equation

HRID 719067 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6]Br.[CH:8]12[O:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]2[C:15]([O:17]C)=O.[Cl-].[NH4+]>O1CCCC1>[CH:8]12[O:14][CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]2[C:15]1([OH:17])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 25517Ammonium ChlorideHCID 30435117791-35-4HCID 5462224Magnesium

Product 1

HCID 21896328HCID 21896328, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A flask was charged with 14.6 g of magnesium and 270 ml of tetrahydrofuran, to which 64.8 g of 1,4-dibromobutane was added dropwise at 50° C. After the completion of dropwise addition, the solution was stirred at 60° C. for one hour. To the solution below 40° C., 39.0 g of methyl 7-oxa-2-norbornanecarboxylate was added dropwise. The solution was stirred at room temperature for one hour, after which an aqueous solution of ammonium chloride was added for hydrolysis. Ordinary post-treatment yielded 43.7 g of 1-(7-oxanorbornan-2-yl)cyclopentanol.

Workup

  1. additionwas added dropwise at 50° C
  2. additionAfter the completion of dropwise addition
  3. stirringThe solution was stirred at room temperature for one hour

Sources & evidence

ORD record
ord-57115570e0ae4f50a5552020611b0614
Source dataset
uspto-grants-2006_11
Patent number
US07132215B2

Reaction notes

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