Dimethyl Sulfoxide → 2-Bromo-5-chlorothiophene-3-carbaldehyde

HRID 870030Notes

Reaction equation

HRID 870030 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[S:13][C:14]([Cl:19])=[CH:15][C:16]=1[CH2:17][OH:18].C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[S:13][C:14]([Cl:19])=[CH:15][C:16]=1[CH:17]=[O:18]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57900970(2-Bromo-5-chlorothiophen-3-yl)methanol

Product 1

HCID 509991562-Bromo-5-chlorothiophene-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DMSO (2.10 mL, 29.7 mmol) in dichloromethane (50 mL) at −78° C. was added oxalyl chloride (1.90 mL, 26.8 mmol) dropwise and the mixture was stirred for 30 min. at the temperature. To it was then added (2-bromo-5-chloro-3-thienyl)methanol from Example 1, Step 2 (4.50 g, 19.8 mmol, crude) in dichloromethane (25 mL) via a cannula and the resultant solution was stirred for 30 min. Triethylamine (6.40 mL, 45.5 mmol) was added in one portion and the mixture was stirred at −78° C. for 30 min. and allowed to warm slowly in air. The mixture was concentrated in vacuo and then resuspended in ether and then filtered. The filtrate was concentrated in vacuo to give the desired product. The crude was used directly without further purification.

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min.
  2. temperatureto warm slowly in air
  3. concentrationThe mixture was concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b7e78f9b57464da1a2d4f9cbfb5c49a6
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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