Bromine → Dibenzyl bromopropanedioate

HRID 1445906Notes

Reaction equation

HRID 1445906 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[Br:22]Br>C(Cl)(Cl)(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([Br:22])[C:1]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 84754Dibenzyl malonate

Product 1

HCID 15178112Dibenzyl bromopropanedioate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of dibenzyl malonate (9.8 g, 34.46 mmole) in carbon tetrachloride (25 mL), bromine (10.14 g, 63.4 mmole) was added dropwise at room temperature over 4 h. The reaction mixture was irradiated with a 150 W lamp during the addition. The reaction mixture was quenched with water. The organic layer was separated and the aqueous layer was further extracted with dichloromethane (3 ×30 mL). The organic extracts were combined, washed with sodium hydrogen carbonate solution (3×50 mL) and brine solution 3×50 mL). The organic layer was dried over magnesium sulphate and concentrated. The residue was purified by column chromatography (9:1 Hex:EtOAc) to afford intermediate 2 as an orange oil. Yield 3.8 g, 30%

Workup

  1. customThe reaction mixture was irradiated with a 150 W lamp during the addition
  2. customThe reaction mixture was quenched with water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was further extracted with dichloromethane (3 ×30 mL)
  5. washwashed with sodium hydrogen carbonate solution (3×50 mL) and brine solution 3×50 mL)
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (9:1 Hex:EtOAc)

Sources & evidence

ORD record
ord-74e0fea6de704a96a1ce6503f74abf40
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Reaction notes

Loading…