Hydrochloric Acid → HCID 54550811, compound

HRID 266595Notes

Reaction equation

HRID 266595 reaction equation
[CH2:1]([OH:6])[C:2]([F:5])([F:4])[F:3].[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH2:18]Br)[CH:9]=1.Cl>CN(C=O)C>[Br:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([CH2:18][O:6][CH2:1][C:2]([F:5])([F:4])[F:3])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 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 Nail (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. 0.5M 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-0dfa714f89dc4f51aa7a9e1a48e94997
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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