Tetrahydrofuran → HCID 14043443, compound

HRID 1199857Notes

Reaction equation

HRID 1199857 reaction equation
Br[CH2:2][CH:3]=[C:4]([F:10])[C:5]([O:8][CH3:9])(F)F.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[O:19]1CCCC1>C(OCC)C>[F:10]/[C:4](=[CH:3]\[CH2:2][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:5]([O:8][CH3:9])=[O:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 54329401HCID 54329401, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 14043443HCID 14043443, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1.0 g (4.5 mmol) 4-bromo-1-methoxy-1,1,2-trifluoro-2-butene in 15.0 mL tetrahydrofuran at -60° C. was added a solution of phenylmagnesium bromide (3M, 1.6 mL, 4.8 mmol) in diethyl ether and the mixture was stirred for 1 hr. at -60° C. then stirred for 12 hours at 20° C. The workup and acidic hydrolysis was done as mentioned in Example 3 to give 0.34 g (42%) of methyl (Z)-2-fluoro-4-phenyl-2-butenoate. 1H-NMR (300 MHz, CDCl3): δ 3.58(2H, dd, J=2, 9Hz), 3.81(3H, s), 6.29(1H, dt, J=9, 31 Hz), 7.18-7.34(5H, m). Mass spectrum: m/e=194 (M+). 19F-NMR (CDCl3): φ 131.3(d, J=31.1 Hz).

Workup

  1. stirringat -60° C. then stirred for 12 hours at 20° C
  2. customThe workup and acidic hydrolysis

Sources & evidence

ORD record
ord-7dbdca7abc7948c8b9ce2d30a6c43877
Source dataset
uspto-grants-1990_02
Patent number
US04902835

Reaction notes

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