Methyl iodide → Methyl 2-(2-fluorophenyl)propanoate

HRID 1600835Notes

Reaction equation

HRID 1600835 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[Li+].[CH3:14]C([N-]C(C)C)C.CI.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:14])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 2733230Methyl 2-fluorophenylacetate

Product 1

HCID 21830852Methyl 2-(2-fluorophenyl)propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 2-fluorophenylacetate (24.2 g, 0.144 mol) in THF (75 ml) was added dropwise over 20 min to a -78° C. solution of LDA (diisopropylamine (16.0 g, 0.158 mol) and n-butyl lithium (2.5 M, 61 ml)) in THF (300 ml) and stirring was continued for 1 h. Methyl iodide (22.5 g, 0.158 mol) was added dropwise over 15 min and the reaction mixture allowed to warm to room temperature over 1 h. The solution was poured into saturated ammonium chloride solution and extracted with diethyl ether. The extract was washed with brine, dried and evaporated to yield methyl 2-(2-fluorophenyl)propanoate (26.2 g, 100%) as an oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-dedc561ebd244235ac9faf8b78884e32
Source dataset
uspto-grants-1999_11
Patent number
US05977116

Reaction notes

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