Dibromomethane → HCID 13069837, compound

HRID 1703166Notes

Reaction equation

HRID 1703166 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH:21]1[CH2:26][CH:25]([CH2:27][CH3:28])[O:24][C:22]1=[O:23].[Br:29][CH2:30]Br>CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>[Br:29][CH2:30][C:21]1([C:15]2[CH:16]=[CH:17][C:18]([Cl:20])=[CH:19][C:14]=2[Cl:13])[CH2:26][CH:25]([CH2:27][CH3:28])[O:24][C:22]1=[O:23]

Participants

7

Reactant 4

HCID 3024DibromomethaneHCID 7912DiisopropylamineHCID 13069836HCID 13069836, compoundHCID 178418339Butyllithium

Product 1

HCID 13069837HCID 13069837, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 14.8 g. (0.23 m) diisopropylamine in 100 ml. of dry tetrahydrofuran is added 14.8 g. (023 m) n-butyllithium at -60° C. under nitrogen. Stirring is continued for 15 minutes when a solution of 50 g. (0.19 m) 2-(2,4-dichlorophenyl)-4-ethyl-gamma-butyrolactone in 75 ml. of tetrahydrofuran is added dropwise in one hour. The resulting mixture is further stirred for an addition 1/2 hour when the temperature is raised to -40° C. and a solution of 40.3 g. (0.23 m) dibromomethane and 41.5 g. (0.23 m) hexamethylphosphoramide is added dropwise in 45 minutes. The reaction mixture is stirred at room temperature overnight. It is then poured into 500 ml. of saturated ammonium chloride solution and extracted with ether. The combined ether extracts are dried over sodium sulfate and filtered. The solvent is removed under vacuum and the residue is further purified by vacuum distillation (158° C./0.1 mm) to give 47 g. of a yellow oil.

Workup

  1. customat -60° C.
  2. stirringThe resulting mixture is further stirred for an addition 1/2 hour when the temperature
  3. stirringThe reaction mixture is stirred at room temperature overnight
  4. additionIt is then poured into 500 ml
  5. extractionof saturated ammonium chloride solution and extracted with ether
  6. dry with materialThe combined ether extracts are dried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent is removed under vacuum
  9. distillationthe residue is further purified by vacuum distillation (158° C./0.1 mm)
  10. customto give 47 g

Sources & evidence

ORD record
ord-3980c22a9f104aa29993d58064e2e5c5
Source dataset
uspto-grants-1982_09
Patent number
US04351839

Reaction notes

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