Benzyl mercaptan → 5-(Benzylthio)-2-fluorobenzonitrile
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C(N(CC)C(C)C)(C)C.[CH2:20]([SH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.[Pd+2].ClC1C=C[C-](P(C(C)(C)C)C(C)(C)C)C=1Cl.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2]>[CH2:20]([S:27][C:2]1[CH:3]=[CH:4][C:5]([F:10])=[C:6]([CH:9]=1)[C:7]#[N:8])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
To a degassed solution of 5-bromo-2-fluorobenzonitrile (10 g, 50 mmol) in toluene (250 mL) was added N,N-diisopropylethylamine (26 mL, 150 mmol), benzyl mercaptan (5.87 mL, 52 mmol) and dichloro[1,1′ bis(di-tert-butylphosphino)]ferrocene palladium (II) (500 mg, 1 mmol). The reaction mixture was heated at 60° C. for 16 hours. The reaction mixture was diluted to 500 mL volume with ethyl acetate and washed with dilute brine (300 mL), then 2N HCl (2×300 mL) and finally dilute brine (300 mL). The combined organic layers were dried over MgSO4, filtered and the solvent removed in vacuo. The residue was purified using silica gel column chromatography eluting with 10% ethyl acetate in heptane to afford the title compound as light brown solid (6.18 g, 51%)
Workup
- washwashed with dilute brine (300 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- customthe solvent removed in vacuo
- customThe residue was purified
- washeluting with 10% ethyl acetate in heptane
Sources & evidence
- ORD record
- ord-5e49ee071af34da9a19c870be9e09b35
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067922B2
Reaction notes
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