Bromine → HCID 21329487, compound

HRID 839457Notes

Reaction equation

HRID 839457 reaction equation
[H-].[Na+].[CH3:3][CH:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[Br:19]Br>O1CCCC1.ClCCl>[Br:19][C:4]([CH3:3])([C:5]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:6])[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13]

Participants

6

Reactant 3

HCID 24408BromineHCID 24758Sodium hydrideHCID 12530063Di-tert-butyl methylpropanedioate

Product 1

HCID 21329487HCID 21329487, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of sodium hydride (1.7g, 80% dispersion in oil) in tetrahydrofuran (60 ml) under an atmosphere of nitrogen was added di-t-butyl methylmalonate (11.52g). The mixture was stirred at 60°-70° for 1.5 hours to give a clear solution. This solution was cooled to -25°, and to it was rapidly added a solution of bromine (2.6 ml) in dichloromethane (30 ml). The solution was allowed to warm to ambient temperature, then concentrated. The residue in ether was washed with water, dried, and fractionally distilled under reduced pressure to give the title compound b.p. 78°-86°/1.0 mm Hg, (7.56g, 49%); vmax (CHBr3) 1730cm-1 (CO2But); τ (CDCl3) values include 8.05 (s, C(CH3)3) and 8.53 (2s, CH3 and C(CH3)3).

Workup

  1. customto give a clear solution
  2. temperatureThis solution was cooled to -25°
  3. concentrationconcentrated
  4. washThe residue in ether was washed with water
  5. customdried
  6. distillationfractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-ba49fd7329554e34a5acf15c270f60ed
Source dataset
uspto-grants-1978_06
Patent number
US04095021

Reaction notes

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