Allyl bromide → HCID 57437443, compound

HRID 2240835Notes

Reaction equation

HRID 2240835 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:4][C:3]=1[CH3:15].[CH2:16](Br)[CH:17]=[CH2:18]>C1COCC1>[CH2:18]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:4][C:3]=1[CH3:15])[CH:17]=[CH2:16]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 57437442HCID 57437442, compound

Product 1

HCID 57437443HCID 57437443, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

The corresponding Grignard-reagent is prepared form 2-(4-bromo-3,5-dimethyl-phenyl)-[1,3]dioxane (2.5 g, 9.22 mmol) and Mg (258 mg, 10.6 mmol) in THF (50 mL). To this reagent allylbromide (1.23 g, 10.14 mmol) is added dropwise at rt. The reaction mixture becomes warm (40° C.) and it is stirred for 16 h. The reaction is quenched by adding water. The mixture is extracted with EA. The organic extract is dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 10:1 to give 2-(4-allyl-3,5-dimethyl-phenyl)-[1,3]dioxane (1.8 g) as a colourless oil; LC-MS: tR=1.02 min, [M+1]+=233.22, 1H NMR (CDCl3): δ 7.12 (s, 2H), 5.94-5.80 (m, 1H), 5.44 s, 1H), 4.95 (dd, J=1.8, 10.0 Hz, 1H), 4.80 (dd, J=1.8, 17.0 Hz, 1H), 4.30-4.21 (m, 2H), 4.04-3.92 (m, 2H), 3.40-3.34 (m, 2H), 2.32-2.26 (m, 8H).

Workup

  1. customThe reaction is quenched
  2. additionby adding water
  3. extractionThe mixture is extracted with EA
  4. extractionThe organic extract
  5. dry with materialis dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by CC on silica gel eluting with heptane:EA 10:1

Sources & evidence

ORD record
ord-d8ab06358c7f4ff1898e3b389737e28f
Source dataset
uspto-grants-2010_05
Patent number
US07723378B2

Reaction notes

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