Water → HCID 68456746, compound

HRID 1453927Notes

Reaction equation

HRID 1453927 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]3[C:12]([CH2:13]Br)=[CH:11][CH:10]=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:18][SH:19].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:22]([O:21][C:17](=[O:20])[CH2:18][S:19][CH2:13][C:12]1[C:6]2[C:5]3[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][C:4]=3[O:8][C:7]=2[CH:9]=[CH:10][CH:11]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 21931910HCID 21931910, compound2×

Product 1

HCID 68456746HCID 68456746, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-chloro-1-bromomethyl-dibenzofuran (compound 1b; 7.63 g, 25.9 mmole) in 80 ml of DMF, were added ethyl thioglycolate (2.75 g, 25.94 mmole) and potassium carbonate (4 g, 29 mmole). The mixture was kept at 40-50° C. for 30 minutes. Water (500 mL) was added to give a suspension which was extracted by 2×100 mL dichloromethane, the extracts were washed by water, dried over sodium sulfate, evaporated to give 8.9 g of 2-(7-chlorodibenzofuran-1-ylmethylsulfanyl)acetic acid ethyl ester (compound Ia). This compound is pure enough for the next step without further purification.

Workup

  1. customto give a suspension which
  2. extractionwas extracted by 2×100 mL dichloromethane
  3. washthe extracts were washed by water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-27b8509065864f09abe1aee14e2c81a4
Source dataset
uspto-grants-2009_01
Patent number
US07476690B2

Reaction notes

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