Iodobenzene diacetate → 4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzaldehyde

HRID 2281072Notes

Reaction equation

HRID 2281072 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.C(OI(OC(=O)C)C1C=CC=CC=1)(=O)C>ClCCl>[Cl:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]3[CH2:14][CH2:13]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:16]=[CH:17][C:18]([CH:21]=[O:22])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 76724Iodobenzene diacetateHCID 70977671HCID 70977671, compound

Product 1

HCID 867119874-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{4-[4-Chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]phenyl}methanol (Example 29, 50 mg, 0.16 mmol) was dissolved in dichloromethane (1.6 mL) and treated with diacetoxy(phenyl)-iodane (51 mg, 0.16 mmol) and (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (2.5 mg, 0.016 mmol). The mixture was stirred at ambient tempuratures for 16 hours, diluted with dichloromethane and washed with sodium bicarbonate (2×30 ml, aqueous saturated). The organic extract was dried with sodium sulfate, filtered and concentrated in vacuo to afford the titled compound.

Workup

  1. washwashed with sodium bicarbonate (2×30 ml, aqueous saturated)
  2. extractionThe organic extract
  3. dry with materialwas dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06c076a90be6486cb3fdae78a8c5f71b
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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