2-Bromobenzyl bromide → HCID 10616009, compound

HRID 565426Notes

Reaction equation

HRID 565426 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.C([N-]C(C)C)(C)C.[Li+].[Br:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Br>C1COCC1>[Br:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23][CH:8]1[C:7](=[O:10])[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9]1

Participants

5

Reactant 3

HCID 769652-Bromobenzyl bromideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 10616009HCID 10616009, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 1,4-cyclohexanedione mono-ethylene acetal (20 g, 28 mmol) in THF (360 ml) is added dropwise under nitrogen to a solution, cooled to −78° C., of 1M lithium diisopropylamide in THF (150 mmol, 150 ml), and the mixture is then allowed to return to room temperature. After stirring for 1 hour, the mixture is cooled to −78° C. and 35.2 g (141 mmol) of 2-bromobenzyl bromide are added dropwise. After stirring for 30 minutes at −78° C., the temperature of the mixture is returned to 0° C. The mixture is stirred for 3 hours at 0° C. and then hydrolysed and extracted with ether. The organic phase is washed with a saturated NaCl solution, dried over MgSO4 and concentrated in vacuo. The title compound is purified by flash chromatography over a column.

Workup

  1. customto return to room temperature
  2. stirringAfter stirring for 30 minutes at −78° C.
  3. customis returned to 0° C
  4. stirringThe mixture is stirred for 3 hours at 0° C.
  5. extractionhydrolysed and extracted with ether
  6. washThe organic phase is washed with a saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe title compound is purified by flash chromatography over a column

Sources & evidence

ORD record
ord-bd0d98731b8c40d3bb0af5429ce650df
Source dataset
uspto-grants-2001_01
Patent number
US06172097B2

Reaction notes

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