Allyl bromide → HCID 13957748, compound

HRID 2308922Notes

Reaction equation

HRID 2308922 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3]C.C(NC(C)C)(C)C.[F:13][C:14]([F:37])([F:36])[C:15]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH3:26])[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:17]([C:32]([F:35])([F:34])[F:33])[N:16]=1.C(Br)C=C>O1CCCC1>[F:37][C:14]([F:13])([F:36])[C:15]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH2:26][CH2:3][CH:2]=[CH2:1])[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:17]([C:32]([F:34])([F:33])[F:35])[N:16]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 13957658HCID 13957658, compoundHCID 178418339Butyllithium

Product 1

HCID 13957748HCID 13957748, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A three-necked 250 ml flask is heated, desiccated, and purged with argon. Tetrahydrofuran (50 ml) is injected via syringe and the flask is cooled to -78° C. To this is added 8.33 ml (0.0133 mole) of 1.6M n-butyl lithium via syringe followed by 2 ml (0.0133 mole) of diisopropyl amine. To 10 ml of dried tetrahydrofuran, 5 g (0.0133 mole) of the product of Example 2 is added and the solution is injected into the reaction mixture. The mixture is stirred for an hour. Allyl bromide, 2.4 g (0.02 mole) is injected into the flask and the mixture is stirred for 90 minutes at room temperature.

Workup

  1. temperatureA three-necked 250 ml flask is heated
  2. custompurged with argon
  3. customTetrahydrofuran (50 ml) is injected via syringe
  4. stirringthe mixture is stirred for 90 minutes at room temperature

Sources & evidence

ORD record
ord-4caacf7144bc4a34818875e41cc9cd65
Source dataset
uspto-grants-1987_09
Patent number
US04692184

Reaction notes

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