5-Bromo-4-chloro-2-fluoro-n-methyl-n-o-tolyl-benzamide → 5-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide

HRID 448897Notes

Reaction equation

HRID 448897 reaction equation
[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5](F)=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8].[CH3:21][O:22][Na].CO>>[Br:1][C:2]1[C:3]([Cl:20])=[CH:4][C:5]([O:22][CH3:21])=[C:6]([CH:18]=1)[C:7]([N:9]([CH3:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:8]

Participants

3

Reactant 2

HCID 686027675-Bromo-4-chloro-2-fluoro-n-methyl-n-o-tolyl-benzamideHCID 178501943HCID 178501943, compound

Product 1

HCID 686036055-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide

Procedure

A mixture of 5-bromo-4-chloro-2-fluoro-N-methyl-N-o-tolyl-benzamide (2.5 g, 7.0 mmol) was heated in MeONa/MeOH (20 mL, 25%) at 55° C. for 12 hrs, then was concentrated and partitioned between DCM and water. The organic layer was then separated, washed with 3N HCl, sat NaHCO3 and brine, dried over MgSO4, and concentrated. Purification by silica gel column chromatography eluting with ethyl acetate in hexanes (1/4) gave 5-bromo-4-chloro-2-methoxy-N-methyl-N-o-tolyl-benzamide (2.75 g). MS: 367.8 (M+H)+; tR=2.51 min (method 1).

Workup

  1. concentrationwas concentrated
  2. custompartitioned between DCM and water
  3. customThe organic layer was then separated
  4. washwashed with 3N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customPurification by silica gel column chromatography
  8. washeluting with ethyl acetate in hexanes (1/4)

Sources & evidence

ORD record
ord-852b99300976438c96131f4d445fb822
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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