Allyl bromide → Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

HRID 451518Notes

Reaction equation

HRID 451518 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([O:12][CH3:13])=[O:11].[CH2:14](Br)[CH:15]=[CH2:16]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:16][CH:15]=[CH2:14])[C:10]([O:12][CH3:13])=[O:11]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 736123(2-Chloro-4-fluorophenyl)acetic acid methyl ester

Product 1

HCID 67342147Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled (−78° C.) solution of lithium hexamethydisilylazide (27.1 mL, 1 M in THF, 27.1 mmol) in THF (30 mL) was added methyl 2-(2-chloro-4-fluorophenyl)acetate (5 g, 24.7 mmol) in THF (10 mL). After stirring for 0.5 hour, allyl bromide (2.4 mL, 27.1 mmol) was added in a single portion, the cooling bath removed and the reaction allowed to warm to room temperature (0.5 hour). The reaction was diluted with ethyl acetate, washed with water, brine, and the organic phase was dried with sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 1:0 to 9:1) as eluent. The title compound was obtained as a colourless liquid (6.0 g, 100%).

Workup

  1. customthe cooling bath removed
  2. additionThe reaction was diluted with ethyl acetate
  3. washwashed with water, brine
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4e326ceebe6c49219fba7618bae5416d
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…