Dimethylformamide → Benzo(b)thiophene-3-carbonyl chloride

HRID 408627Notes

Reaction equation

HRID 408627 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1C(O)=O.CN(C=O)C.C(Cl)(=O)[C:19]([Cl:21])=[O:20]>CC1OCCC1>[S:1]1[CH:2]=[C:3]([C:19]([Cl:21])=[O:20])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 95864Benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 2776338Benzo(b)thiophene-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To benzothiophene carboxylic acid (7 g) in MeTHF (6.5 Vols, 45.5 mL) is added a catalytic amount of DMF (0.01 eq.). Then, oxalyl chloride (1.1 eq.) is charged slowly to control the gaz release. After 16 h of stirring at 20° C., the end of the reaction is controlled by HPLC. MeTHF (6.5 Vols) is next added and the reaction mixture is concentrated to 5 volumes to remove the excess of oxalyl chloride. The resulting benzo[b]thiophene-3-carbonyl chloride is stored in a MeTHF solution.

Workup

  1. concentrationthe reaction mixture is concentrated to 5 volumes
  2. customto remove the excess of oxalyl chloride

Sources & evidence

ORD record
ord-6d18a7e0852447e48ad0e4650ed05b99
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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