Sodium Carbonate → Ethyl 2-(4'-cyanobiphenyl-2-ylthio)-2-methylpropanoate

HRID 1503091Notes

Reaction equation

HRID 1503091 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]([CH3:14])([CH3:13])[C:10]([O-:12])=[O:11].[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)#[N:16].C(=O)([O-])[O-].[Na+].[Na+].O1CCO[CH2:34][CH2:33]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]([C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][C:9]([CH3:14])([CH3:13])[C:10]([O:12][CH2:33][CH3:34])=[O:11])=[CH:19][CH:18]=1)#[N:16]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 27343264-Cyanophenylboronic acidHCID 422050782-(2-Bromophenylthio)-2-methylpropanoate

Product 1

HCID 68001012Ethyl 2-(4'-cyanobiphenyl-2-ylthio)-2-methylpropanoateYield 57%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(2-bromophenylthio)-2-methylpropanoate (151 mg, 0.5 mmol), 4-cyanophenyl boronic acid (76 mg, 0.5 mmol), aqueous sodium carbonate solution (2 M, 1 mL), and Pd(PPh3)4 (29 mg, 0.025 mmol) in dioxane (2 mL) was degassed for 15 minutes. The mixture was sealed and heated to 80° C. for 12 hours. The reaction mixture was washed with water, extracted with ethyl acetate, dried (MgSO4), concentrated and purified by chromatography to yield ethyl 2-(4′-cyanobiphenyl-2-ylthio)-2-methylpropanoate (93 mg, 57%).

Workup

  1. customwas degassed for 15 minutes
  2. customThe mixture was sealed
  3. washThe reaction mixture was washed with water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-93eb1d26402f4238b4106e9e0aaeeedf
Source dataset
uspto-grants-2015_12
Patent number
US09212135B2

Reaction notes

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