Hydrochloric Acid → HCID 54550811, compound

HRID 2256980Notes

Reaction equation

HRID 2256980 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 4-bromo-2-bromomethylbenzoate (3.52 g) in DMF was added, and the resultant mixture stirred at room temperature for 1 hour. 0.5 M 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(dr,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-a4395324ba3e4410ac6e7f815628fdd2
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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