3-Bromo-7-benzothiophene-carbaldehyde → 1-Benzothiophene-7-carbaldehyde

HRID 974375Notes

Reaction equation

HRID 974375 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[O:12])[C:5]=2[S:4][CH:3]=1.[H][H]>[Pd].O1CCCC1.C(N(CC)CC)C>[S:4]1[C:5]2[C:10]([CH:11]=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=2[CH:2]=[CH:3]1

Participants

6

Reactant 2

HCID 199863443-Bromo-7-benzothiophene-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 107021381-Benzothiophene-7-carbaldehyde

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

2 g of 5% palladium-on carbon catalyst are added to a solution of 10.4 g (43.15 mmoles) of 3-bromo-7-benzothiophene-carbaldehyde in 130 ml of tetrahydrofuran and 5.6 ml of triethylamine and the mixture is hydrogenated with hydrogen in a hydrogenating apparatus for 45 hours at 20°-22° C. under atmospheric pressure. The catalyst is then filtered off and the solvent is evaporated in vacuo from the filtrate. The residue is dissolved with 50 ml each of water and ethyl acetate, and 5.2 g (67.5% of the theoretical amount) of 7-benzothiophene-carbaldehyde are obtainable as residue from the separated organic phase after evaporation of the solvent in vacuo.

Workup

  1. filtrationThe catalyst is then filtered off
  2. customthe solvent is evaporated in vacuo from the filtrate
  3. dissolutionThe residue is dissolved with 50 ml each of water and ethyl acetate, and 5.2 g (67.5% of the theoretical amount) of 7-benzothiophene-carbaldehyde
  4. customafter evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-f48e90632933425393c1a9e8bd72a15e
Source dataset
uspto-grants-1991_11
Patent number
US05068359

Reaction notes

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