Methyl chloroacetate → HCID 19900755, compound

HRID 1439256Notes

Reaction equation

HRID 1439256 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1CC(O)=S.BrC1[S:13]C=CC=1Br.C([Li])CCC.[S].Cl[CH2:25][C:26]([O:28]C)=[O:27]>>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:13][CH2:25][C:26]([OH:28])=[O:27]

Participants

6

Reactant 5

HCID 7295Methyl chloroacetateHCID 765902,3-DibromothiopheneHCID 5362487SulfurHCID 178418339ButyllithiumHCID 178526166HCID 178526166, compound

Product 1

HCID 19900755HCID 19900755, compoundYield 76%

Procedure

The compound is prepared analogously to Example 10 by saponification of the crude methyl ester of (3-bromo-2-thienylthio-acetic acid prepared with a 76% yield from 2,3-dibromothiophene, butyllithium, sulfur, and methyl chloroacetate. After chromatography on silica gel (eluent: hexane/acetone/acetic acid = 93:5:2), the product is obtained as a non-crystallizing oil. The compound shows the physiochemical data to be expected (IR, NMR spectrum) and yields correct elementary analyses for C, H, S, and Br.

Workup

  1. customAfter chromatography on silica gel (eluent: hexane/acetone/acetic acid = 93:5:2), the product is obtained as a non-crystallizing oil
  2. customyields correct elementary analyses for C, H, S, and Br

Sources & evidence

ORD record
ord-47f052e3f1364218adfb388046fb1497
Source dataset
uspto-grants-1977_11
Patent number
US04058619

Reaction notes

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