3-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide → 3-bromo-4-formyl-N-(3-(trifluoromethyl)phenyl)benzamide

HRID 594085

Reaction equation

HRID 594085 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH2:21][OH:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6]>C(Cl)Cl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH:21]=[O:22])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:16])([F:17])[F:15])[CH:9]=1)=[O:6]

Participants

4

Reactant 1

HCID 904079633-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 904087973-bromo-4-formyl-N-(3-(trifluoromethyl)phenyl)benzamideYield 100%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

MnO2 (8.0 equiv.) was added into a solution of 3-bromo-4-(hydroxymethyl)-N-(3-(trifluoromethyl)phenyl)benzamide (1.0 equiv.) in DCM (0.14 M). The suspension was stirred at rt for 1 hr. The mixture was filtered over celite and concentrated to yield 3-bromo-4-formyl-N-(3-(trifluoromethyl)phenyl)benzamide in 100% yield. LC/MS (m/z)=373.9 (MH+), Rt=0.0.94 min.

Workup

  1. filtrationThe mixture was filtered over celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4e48c0fa86af45f8b79503bd0b7583b0
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Linked notes

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