Hydrochloric Acid → HCID 54550811, compound

HRID 343036Notes

Reaction equation

HRID 343036 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[Br:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH2:20]Br)[CH:11]=1.Cl>CN(C=O)C>[Br:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([CH2:20][O:8][CH2:3][C:4]([F:7])([F:6])[F:5])[CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 54550811HCID 54550811, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (0.5 g of 60% dispersion in oil) in DMF (10 ml) was added trifluoroethanol (0.92 ml) and the mixture stirred for 30 minutes. After this time the mixture was cooled to 0° C. and a solution of methyl 4bromo-2-bromomethylbenzoate (3.52 g) in DMF was added, and the resultant mixture stirred at room temperature for 1 hour. 0.5M HCl was added and the mixture extracted with ether. The organic extract was washed with water, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness to yield methyl 4-bromo-2-trifluoroethoxymethylbenzoate (3.89 g) as a yellow oil, NMR (CDCl3) 3.9(s,3H), 4.0(q,2H), 5.1(s,2H), 7.5(dd,1H), 7.85(d,1H), 7.9(s,1H).

Workup

  1. extractionthe mixture extracted with ether
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-f4df3f93e2d44d4baf0d2b27ceed1d34
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

Loading…