Allyl bromide → HCID 59324097, compound

HRID 1639710Notes

Reaction equation

HRID 1639710 reaction equation
[C:1]([Li])(C)([CH3:3])[CH3:2].CCCCC.CC1C=C(C)C=C(C)C=1Br.[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][N:30]=[C:29]1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[CH3:42])=[O:27])([CH3:24])([CH3:23])[CH3:22].C(Br)C=C>C1COCC1.O.CCOC(C)=O.C(O)(=O)C>[C:21]([O:25][C:26]([N:28]1[CH2:32][CH2:31][N:30]=[C:29]1[CH:33]([O:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[C:36]=1[CH3:42])[CH2:3][CH:1]=[CH2:2])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

10

Reactant 5

HCID 7841Allyl bromideHCID 8003PentaneHCID 684732-BromomesityleneHCID 59324098HCID 59324098, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59324097HCID 59324097, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of t-butyllithium in pentane (1.7M, 5.7 ml, 9.84 mmol) was added in portions to a solution of 2,4,6-trimethylphenylbromide (0.744 ml, 980 mg, 4.93 mmol) in 8 ml THF at ca −78° C. A white precipitate was formed. After 10 minutes at low temperature a solution of 2-(2,3-dimethyl-phenoxymethyl)-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester (1 g, 3.28 mmol) in 6 ml THF was added in portions to give an orange solution. This was warmed to −20° C. and cooled again to ca −70° C. whereupon much of the solid went into solution. Allyl bromide (0.332 ml, 475 mg, 3.93 mmol) was added and the reaction mixture stirred for 30 min at this temperature before a small amount of acetic acid was added. The mixture was warmed and shaken between EtOAc and water. The organic phase was dried with Na2SO4 and evaporated to give 1.3 g of crude product, which was chromatographed on silica to yield 2-[1-(2,3-dimethyl-phenoxy)-but-3-enyl]-4,5-dihydro-imidazole-1-carboxylic acid tert-butyl ester. 1H-NMR (CDCl3) (selection) 5.10 (d, allyl), 5.18 (d, allyl), 5.66 (t, OCH), 5.98 (m, allyl)

Workup

  1. customA white precipitate was formed
  2. customto give an orange solution
  3. temperaturecooled again to ca −70° C. whereupon much of the solid
  4. additionwas added
  5. temperatureThe mixture was warmed
  6. dry with materialThe organic phase was dried with Na2SO4
  7. customevaporated
  8. customto give 1.3 g of crude product, which
  9. customwas chromatographed on silica

Sources & evidence

ORD record
ord-0a2d31df221f4c8cbf9499811a7c63bf
Source dataset
uspto-grants-2012_02
Patent number
US08110593B2

Reaction notes

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