1-Bromo-3-chloropropane → HCID 20096925, compound

HRID 1769675Notes

Reaction equation

HRID 1769675 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[Li]CCCC.[Li+].CC([N-]C(C)C)C.[Cl:32][CH2:33][CH2:34][CH2:35]Br.[NH4+].[Cl-]>C1COCC1>[C:7]1([C:5]2[N:6]=[C:2]([CH2:1][CH2:35][CH2:34][CH2:33][Cl:32])[O:3][C:4]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 80061-Bromo-3-chloropropaneHCID 25517Ammonium ChlorideHCID 139703Oxazole, 2-methyl-4,5-diphenyl-HCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 20096925HCID 20096925, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl 4,5-diphenyloxazole (7.05 g, 0.3 mol) in 50 mL of dry THF at -78° C. was added 1.1 equivalent of n-BuLi or LDA and stirred for 30 min. To the dark red solution of the anion was added the alkylating reagent 3-chloro-1-bromopropane (1.1 equivalent) and the reaction mixture was allowed to warm to 0° C. over a period of 1 h. The reaction was worked up by adding NH4Cl solution and extracting with ethyl acetate (50mL). Dried over Na2SO4, concentrated and purified by flash chromatography over silica gel using ether/hexane 1:4 as an eluant to give the Formula X compound 6.2 g (66%) as an oil. MS (DCI) m/z 311.

Workup

  1. extractionextracting with ethyl acetate (50mL)
  2. dry with materialDried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-18202bfadeae4861af86c1136a09ab88
Source dataset
uspto-grants-1995_01
Patent number
US05382584

Reaction notes

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