Triethylamine → 3-Iodo-4-methylbenzonitrile

HRID 1619137Notes

Reaction equation

HRID 1619137 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[I:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18]([NH2:20])=O.C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[I:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:18]#[N:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 8333293-iodo-4-methylbenzamide

Product 1

HCID 121296213-Iodo-4-methylbenzonitrileYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,2,2-trifluoroacetic anhydride (8.00 mL, 57.5 mmol) was added dropwise to a stirred solution of 3-iodo-4-methylbenzamide (preparation 48a, 6.00 g, 23.0 mmol) and triethylamine (8.10 mL, 57.5 mmol) in dichloromethane (50 mL) at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. Further dichloromethane and saturated aqueous potassium carbonate solution were added and the organic layer was washed with 2M aqueous hydrochloric acid, 2M aqueous sodium hydroxide solution, brine, dried (MgSO4) and evaporated to give the title compound (4.50 g, 80%) as a pale orange solid.

Workup

  1. washthe organic layer was washed with 2M aqueous hydrochloric acid, 2M aqueous sodium hydroxide solution, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-bc79983383474776b1875e5879140fdf
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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