Iodine → HCID 59133070, compound

HRID 643430Notes

Reaction equation

HRID 643430 reaction equation
[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:15])[O:12][CH2:13][CH3:14].[I:18]I>C1CCCCC1.C1COCC1>[CH2:13]([O:12][C:11](=[O:15])[NH:10][C:5]1[C:4]([O:3][C:2]([F:16])([F:17])[F:1])=[CH:9][CH:8]=[CH:7][C:6]=1[I:18])[CH3:14]

Participants

5

Reactant 2

HCID 807IodineHCID 2781632ethyl N-[2-(trifluoromethoxy)phenyl]carbamate

Product 1

HCID 59133070HCID 59133070, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8078CyclohexaneSolvent

Procedure

A 1.4 M solution of sec-buthyllithium in cyclohexane (3.0 mL) was added drop-wise to a solution of ethyl N-[2-(trifluoromethoxy)phenyl]carbamate (0.5000 g, 0.002006 mol) in THF (9 mL) at −70° C. After stirring for 1 hour a solution of iodine (0.51 g, 0.002 mol) in THF (1.0 mL) was added drop-wise at −70° C. Stirring was continued for another 1 hour then the mixture was quenched with saturated ammonium chloride solution. Water (50 mL) was added and the mixture extracted with diethyl ether (3×40 mL). The combined organic phases was washed with 40% sodium meta-bisulfite solution, water and brine, then dried over Na2SO4 and the solvent removed in vacuo to give the desired product in a 73% yield. 1H NMR (400 MHz, CDCl3): δ 1.29-1.36 (m, 3H), 4.21-4.28 (m, 2H), 6.21 (br, 1H), 7.05 (t, J=8.0 Hz, 1H), 7.30 (m, 1H) and 7.80 (dd, J=6.8, 1.2 Hz, 1H). MS (ES+): m/z 375.78 [MH+].

Workup

  1. additionwas added drop-wise at −70° C
  2. customthe mixture was quenched with saturated ammonium chloride solution
  3. additionWater (50 mL) was added
  4. extractionthe mixture extracted with diethyl ether (3×40 mL)
  5. washThe combined organic phases was washed with 40% sodium meta-bisulfite solution, water and brine
  6. dry with materialdried over Na2SO4
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-7188395f4af04202bdbaffcc80338c55
Source dataset
uspto-grants-2010_04
Patent number
US07700594B2

Reaction notes

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