Dimethylformamide → 6-Chlorobenzo[b]thiophene-2-carboxaldehyde

HRID 1432840Notes

Reaction equation

HRID 1432840 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[Li]CCCC.CN([CH:19]=[O:20])C.[NH4+].[Cl-]>C1COCC1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([CH:19]=[O:20])[S:7][C:6]=2[CH:10]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 123986016-Chloro-1-benzothiopheneHCID 178418339Butyllithium

Product 1

HCID 178426206-Chlorobenzo[b]thiophene-2-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-chlorobenzo[b]thiophene (1.0 g, 5.93 mmol) in THF (60 mL) at −78° C. is added a 1.6 M solution of n-BuLi in THF (3.9 mL, 6.23 mmol). After 10 minutes, 0.5 mL of DMF is added. The solution is stirred for 0.5 hours, then allowed to warm to ambient temperature. The solution is poured into a solution of saturated NH4Cl. The solution is diluted with ether and the layers are separated. The organic layer is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The title compound is obtained as a white solid. MS (EI): m/z 196 (M+).

Workup

  1. customthe layers are separated
  2. washThe organic layer is washed with H2O and saturated NaCl
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-98111bd695c24282bd84c6168de89b45
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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