2,2,2-Trifluoro-1-methoxyethanol → 4-bromo-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

HRID 554713Notes

Reaction equation

HRID 554713 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[F:11][C:12]([F:18])([F:17])[CH:13](OC)[OH:14]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:8][CH:13]([OH:14])[C:12]([F:18])([F:17])[F:11])=[O:7])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 696834-Bromobenzamide

Product 1

HCID 159065104-bromo-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide

Conditions

Temperature
100 °C

Procedure

was prepared by use of 2,2,-trifluoro-1-methoxy-ethanol in place of chloral in the general method set forth above with the following procedural changes: A mixture of 4-bromobenzamide (0.78 g, 3.9 mmol) and 2,2,2-trifluoro-1-methoxy-ethanol (0.51 mL, 4.3 mmol) was heated at 100° C. for 18 hours. The mixture was evaporated and the residue was diluted with chloroform and concentrated onto silica gel. The product was purified on a SiO2 MPLC column with 1% MeOH:CH2Cl2 to yield the intermediate 4-bromo-N-(2,2,2-trifluoro-1-hydroxyethyl)benzamide, which was used in the general method set forth above to prepare Compound 13.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with chloroform
  3. concentrationconcentrated onto silica gel
  4. customThe product was purified on a SiO2 MPLC column with 1% MeOH

Sources & evidence

ORD record
ord-68a70953c87f4db08aa8a73b8216cb42
Source dataset
uspto-grants-2011_11
Patent number
US08049037B2

Reaction notes

Loading…