1,2-Dibromoethane → HCID 11637164, compound

HRID 1868354Notes

Reaction equation

HRID 1868354 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:16][CH2:17]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:14][O:13][C:10]1[C:11]2[O:12][CH2:16][CH2:17][O:1][C:2]=2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 11694090Methyl 2,3-dihydroxy-4-methoxybenzoate

Product 1

HCID 11637164HCID 11637164, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2,3-dihydroxy-4-methoxybenzoate (0.176 mol), 1,2-dibromo-ethane (0.282 mol), K2CO3 (0.444 mol) and CuO (1.4 g) in DMF (1000 ml) was stirred for 6 hours, cooled, filtered and the filtrate was evaporated. Water (300 ml) was added. The mixture was extracted twice with DCM (300 ml). The organic layer was separated, washed with a saturated NaHCO3 solution, dried, filtered and the solvent was evaporated. The residue was triturated in DIPE. The precipitate was filtered off and dried, yielding 32.1 g of methyl 2,3-dihydro-8-methoxy-1,4-benzodioxin-5-carboxylate (intermediate 1, mp. 84° C.).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customthe filtrate was evaporated
  4. additionWater (300 ml) was added
  5. extractionThe mixture was extracted twice with DCM (300 ml)
  6. customThe organic layer was separated
  7. washwashed with a saturated NaHCO3 solution
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was triturated in DIPE
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-3dec537237794b5d927b08d75911c7ef
Source dataset
uspto-grants-2009_12
Patent number
US07635706B2

Reaction notes

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