Hydrochloric Acid → 4-Benzyloxy-2-iodo-5-methoxybenzonitrile

HRID 2381231Notes

Reaction equation

HRID 2381231 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([CH:13]=[N:14]O)=[C:11]([I:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>C(OCC)(=O)C.O1CCCC1>[CH2:1]([O:8][C:9]1[C:17]([O:18][CH3:19])=[CH:16][C:12]([C:13]#[N:14])=[C:11]([I:20])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 72327488HCID 72327488, compound

Product 1

HCID 671104514-Benzyloxy-2-iodo-5-methoxybenzonitrileYield 51.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-benzyloxy-2-iodo-5-methoxybenzaldehyde oxime (reference example 2-1)(20.8 g), triethylamine (22.7 mL) and tetrahydrofuran (181 mL) was added trifluoroacetic anhydride (23 mL) under ice-bath cooling. After stirring at room temperature for an hour, 2 mol/L hydrochloric acid and ethyl acetate were added to the mixture. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with methanol to give the title compound (10.25 g).

Workup

  1. temperaturecooling
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-4a5f0fc68c5f4cd78fffc49007c50fdb
Source dataset
uspto-grants-2012_09
Patent number
US08258162B2

Reaction notes

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