Pivaloyl chloride → HCID 3702406, compound

HRID 1783899Notes

Reaction equation

HRID 1783899 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]([CH3:18])([CH3:17])[C:14](Cl)=[O:15]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14](=[O:15])[C:13]([CH3:18])([CH3:17])[CH3:12])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 2

HCID 62493Pivaloyl chlorideHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 3702406HCID 3702406, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Fluoro-3-nitroaniline (500 mg, 3.20 mmol) and DMAP (586 mg, 4.80 mmol) were dissolved in 25 mL of DCM. Trimethylacetyl chloride (0.587 mL, 4.80 mmol) was added dropwise and the solution was stirred at rt for 3 h. The solution was washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 35% EtOAc in hexanes as eluent on silica gel to produce the desired title compound. Yield: 713 mg (93%). 1H NMR (400 MHz, CHLOROFORM-D:) δ 1.34 (s, 9H), 7.25 (dd, J=10.25, 9.08 Hz, 1H), 7.50 (br.s, 1H), 7.88 (ddd, J=9.08, 3.71, 2.83 Hz, 1H), 8.26 (dd, J=6.44, 2.73 Hz, 1H).

Workup

  1. washThe solution was washed with 5% KHSO4 solution, saturated NaHCO3 solution, brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-6e11388875cb4d1e9dd3d37e11d95193
Source dataset
uspto-grants-2009_03
Patent number
US07501447B2

Reaction notes

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