1,2-Dibromoethane → HCID 53689643, compound

HRID 1158452Notes

Reaction equation

HRID 1158452 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([OH:11])[C:8]([OH:12])=[C:7]([OH:13])[CH:6]=1)[CH3:2].Br[CH2:16][CH2:17]Br>CN(C=O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]2[O:12][CH2:16][CH2:17][O:13][C:7]=2[CH:6]=1)=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 78391,2-DibromoethaneHCID 13250Ethyl gallate

Product 1

HCID 53689643HCID 53689643, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3,4,5-trihydroxy-benzoic acid ethyl ester (5.00 g, 24.2 mmol) in DMF (70 mL) are added 1,2-dibromoethane (2.13 mL, 24.2 mmol) and CsCO3 (16.9 g, 50.9 mmol) and the mixture is stirred overnight at room temperature and for 5 hrs at 60° C. Extractive work-up with diethyl ether, washing of the organic phase with brine and evaporation gives the crude product as brown oil which is purified by silica gel chromatography (hexane/AcOEt 3:2). The title compound is obtained as a white solid. TLC, Rf (hexane/AcOEt 1:1)=0.27. MS: 223.0 [M−H]+. 1H-NMR (CDCl3): δ 1.40 (t, 3H), 4.3-4.42 (m, 6H), 5.45 (s, 1H), 7.23 (s, 1H), 7.29 (s, 1H) ppm.

Workup

  1. washExtractive work-up with diethyl ether, washing of the organic phase with brine and evaporation
  2. customgives the crude product as brown oil which
  3. customis purified by silica gel chromatography (hexane/AcOEt 3:2)

Sources & evidence

ORD record
ord-e092aa892544461fa9772ca9dcfd1eca
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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