Dimethyl Sulfide → 2-Fluoro-4-(2-hydroxyethyl)benzonitrile

HRID 1187010Notes

Reaction equation

HRID 1187010 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](O)=[O:11])=[CH:5][C:4]=1[F:13])#[N:2].S(C)C>C1COCC1>[F:13][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][OH:11])[CH:7]=[CH:8][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 178328372-(4-Cyano-3-fluorophenyl)acetic acid

Product 1

HCID 666441972-Fluoro-4-(2-hydroxyethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-cyano-3-fluorophenyl)acetic acid (25.6 g, 143 mmol) in 150 mL of dry THF was cooled by ice/water, and then BH3/Me2S (10 M, 15.7 mL, 157 mmol) was added slowly. The reaction was warmed to ambient temperature and stirred overnight. The mixture was quenched with MeOH and concentrated to dryness. The residue was partitioned between water and EtOAc. The organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 2-fluoro-4-(2-hydroxyethyl)benzonitrile. 1H-NMR (400 MHz, CDCl3) δ ppm 7.52˜7.56 (m, 1H), 7.11˜7.15 (m, 2H), 3.89 (t, J=6.3 Hz, 2H), 2.92 (t, J=6.3 Hz, 2H).

Workup

  1. customThe mixture was quenched with MeOH
  2. concentrationconcentrated to dryness
  3. customThe residue was partitioned between water and EtOAc
  4. washThe organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf948f3cc6d1410e97017693f12bd75e
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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