Bromine → HCID 18918462, compound

HRID 864807Notes

Reaction equation

HRID 864807 reaction equation
[C:1]1(=[O:17])[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:6]=2)[C:1]1=[O:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 14181181HCID 14181181, compound

Product 1

HCID 18918462HCID 18918462, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of the product from step (ii) (1.3 g) in chloroform (15 ml) was added dropwise a solution of bromine (0.29 ml) in chloroform (1 ml) and the resulting mixture was stirred for 4 hours. The solvent was evaporated to give an oil. Purification by flash column chromatography on silica, eluting with ethyl acetate/hexane (30:70 v/v) gave methyl 2-bromotetralone-6-oxyacetate (1.55 g) as an oil: NMR (d6DMSO) δ2.3-2.6(m,2H), 2.9-3.1(m,2H), 3.7(s,3H), 4.9(s,2H), 4.9-5.0(m,1H), 6.9-7.0(m,2H), 7.9(d,1H); m/e 313/315(M+H)+Br pattern.

Workup

  1. customThe solvent was evaporated
  2. customto give an oil
  3. customPurification by flash column chromatography on silica
  4. washeluting with ethyl acetate/hexane (30:70 v/v)

Sources & evidence

ORD record
ord-86e0f1fabe284775809c2277cc0f5a80
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Reaction notes

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