Bromine → HCID 12402643, compound

HRID 1369956Notes

Reaction equation

HRID 1369956 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:11][CH2:12][CH2:13][CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Br:16]Br>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]([Br:16])([CH2:11][CH2:12][CH2:13][CH3:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 67244Diethyl butylmalonate

Product 1

HCID 12402643HCID 12402643, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diethyl-n-butylmalonate (32.2 gm) was dissolved in methylene chloride (200 ml) and treated, dropwise, with a solution of bromine (24.0 gm) dissolved in methylene chloride (25 ml). The resultant mixture was stirred (1 hour, room temperature) whereupon an orange coloration persisted. The solvent was removed under vacuum, and the residue distilled under high vacuum to give the desired product as a clear oil (boiling point temperature 105° C. to 110° C.; 36.0 gm). 1H NMR (CDCl3): δ=0.89-0.92 (t, 3H); 1.25-1.29 (t, 6H); 1.35-1.37 (m, 4H); 2.2-2.26 (m, 2H); 4.23-4.29 (q, 4H); m/z=295 and 297 (M+).

Workup

  1. additiontreated
  2. customThe solvent was removed under vacuum
  3. distillationthe residue distilled under high vacuum

Sources & evidence

ORD record
ord-1931dc95315e4999b5f0795fbae5048d
Source dataset
uspto-grants-2003_06
Patent number
US06579982B1

Reaction notes

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