Sulfuric Acid → HCID 14043444, compound

HRID 1199859Notes

Reaction equation

HRID 1199859 reaction equation
S(=O)(=O)(O)[OH:2].[Br:6][CH2:7][CH:8]=[C:9]([F:15])[C:10]([O:13][CH3:14])(F)F>CCCCC>[Br:6][CH2:7]/[CH:8]=[C:9](\[F:15])/[C:10]([O:13][CH3:14])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 54329401HCID 54329401, compound

Product 1

HCID 14043444HCID 14043444, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a mixture of 3.0 g 75% sulfuric acid and 15 mL n-pentane was added 1.0 g (4.6 mmol) 4-bromo-1-methoxy-1,1,2-trifluoro-2-butene at room temperature in a 50 mL round-bottom flask. The resulting mixture was stirred for 48 hours at room temperature. Excess ice water was added and the liquid extracted with diethyl ether. The ether layer was successively washed with water and brine, then dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo gave the crude ester which was purified by chromatography on silica gel to give 0.62 g (68.9%) of methyl (Z)-4-bromo-2-fluoro-2-butenoate. Analytical sample distilled a 90°-92° C. (18 mm Hg). 1H-NMR (300 MHz, CDCl3) δ 3.84(3H, s), 4.40(2H, dd, J=2.5, 9 Hz), 6.35(1H, dt, J=9, 30 Hz). 19F-NMR (CDCl3): φ 122.5(d, J=30.2 Hz).

Workup

  1. extractionthe liquid extracted with diethyl ether
  2. washThe ether layer was successively washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent in vacuo
  5. customgave the crude ester which
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d7f8ce613d81499c9bdae34b67c6a5ac
Source dataset
uspto-grants-1990_02
Patent number
US04902835

Reaction notes

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