3-[3-(Bromomethyl)phenyl]thiophene → HCID 54473318, compound

HRID 2254479Notes

Reaction equation

HRID 2254479 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH2:9]Br)=[CH:2]1.[C:14]([C:19]1[N:20]=[C:21]([SH:24])[S:22][CH:23]=1)(OCC)=[O:15].[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH2:9][S:24][C:21]2[S:22][CH:23]=[C:19]([CH2:14][OH:15])[N:20]=2)=[CH:2]1

Participants

4

Reactant 3

HCID 132459263-[3-(Bromomethyl)phenyl]thiopheneHCID 21226445Aluminium lithium hydrideHCID 178470113HCID 178470113, compound

Product 1

HCID 54473318HCID 54473318, compound

Procedure

The same reaction as in Referential Example 57 is carried out except using 3-(3-thienyl)benzyl bromide [prepared by reducing 3-(3-thienyl)benzaldehyde with sodium borohydride, followed by reacting with phosphorus tribromide] and 4-carboethoxy-2-mercaptothiazole [J. Org. Chem., 25, 1337 (1960)], and the resulting ester compound is reduced with lithium aluminium hydride to give the captioned compound.

Workup

  1. customThe same reaction as in Referential Example 57
  2. customto give the captioned compound

Sources & evidence

ORD record
ord-409a3a1ae6184924a181b6393fdff09d
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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