Nitromethane → 5-Trichloroacetyl-1H-pyrrole-3-carbaldehyde

HRID 2249514Notes

Reaction equation

HRID 2249514 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].C[N+]([O-])=O.Cl[CH:21](Cl)[O:22]C>C(Cl)CCl>[Cl:11][C:2]([Cl:1])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[C:8]([CH:21]=[O:22])[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 6375NitromethaneHCID 21004Methane, dichloromethoxy-HCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 124599775-Trichloroacetyl-1H-pyrrole-3-carbaldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)-ethanone (5.0 g, 23.53 mmol) and AlCl3 (3.8 g, 28.50 mmol) in co-solvents of EDC (20 mL) and MeNO2 (20 mL) was cooled to −10° C. A solution of dichloro-methoxy-methane (3.25 g, 28.27 mmol) in EDC (5 mL) was added fairly rapidly and the mix was then stirred at −10° C. to room temperature for overnight. It was poured over crushed ice, the layer were separated, and the aqueous phase was extracted with CH2Cl2. The combined organic layers were washed, dried over MgSO4, and concentrated, yielding a slightly reddish solid (3.6 g, 64%). 1H NMR (500 MHz, CDCl3) δ10.10 (s, 1H), 10.06 (br, 1H), 7.96 (m, 2H) ppm. MS (ES−): m/e=238 (M−H); LC/Method A/3.15 min.

Workup

  1. additionIt was poured
  2. customover crushed ice
  3. customthe layer were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. washThe combined organic layers were washed
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c747ab97dfc4472cae1e1777a5b2c603
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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