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

HRID 1502067Notes

Reaction equation

HRID 1502067 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.

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-aef7e1b90de04cf5b6a6cda193915444
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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