4-Fluorobenzyl bromide → HCID 59739580, compound

HRID 1192939Notes

Reaction equation

HRID 1192939 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][S:10]([C:13]1[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][N:14]=1)(=[O:12])=[O:11].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1>C1COCC1>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH:9]([S:10]([C:13]1[CH2:17][C:16]([CH3:19])([CH3:18])[O:15][N:14]=1)(=[O:11])=[O:12])[CH2:25][C:24]1[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 11571391HCID 11571391, compound

Product 1

HCID 59739580HCID 59739580, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phosphazene base 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2-lambda5-5,4-lambda5-5-catenadi(phosphazene) (P2-Et) (0.61 ml, 1.6 mmol) was added dropwise to a solution of 3-(2,6-difluoro-phenylmethanesulfonyl)-5,5-dimethyl-4,5-dihydroisoxazole (0.3 g, 1.04 mmol) in THF (2 ml) at room temperature. After 10 minutes 4-fluorobenzyl bromide (0.16 ml, 1.3 mmol) was added dropwise at room temperature and the mixture was stirred for 1 hour. The reaction was quenched by addition of aqueous hydrochloric acid (2M). The mixture was diluted with ethyl acetate and the two phases were separated. The organic phase was washed several times with brine, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.05 of Table 27) as a white solid (405 mg, 98% yield).

Workup

  1. customThe reaction was quenched by addition of aqueous hydrochloric acid (2M)
  2. additionThe mixture was diluted with ethyl acetate
  3. customthe two phases were separated
  4. washThe organic phase was washed several times with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-da1b273756114a9bb91d25fcca778cd5
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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