Allyl bromide → HCID 57437443, compound

HRID 1665973Notes

Reaction equation

HRID 1665973 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-9f54d2a806a541248615971bc7d5facd
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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