Sodium Carbonate → HCID 21685088, compound

HRID 1452454Notes

Reaction equation

HRID 1452454 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:11]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 80271Tri-o-tolylphosphineHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 21685088HCID 21685088, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of benzeneboronic acid (2.05 g, 16.8 mmol), 3-bromomethylbenzonitrile (3 g, 15.3 mmol), dichlorobis(triphenylphosphine)palladium(II) (1.07 g, 1.53 mmol), tri-o-tolylphosphine (0.465 g, 29 mmol) and sodium carbonate (3.08 g, 29 mmol) in aqueous acetonitrile (1:10, 220 mL) was refluxed under nitrogen for 2 hours, cooled to room temperature, concentrated under reduced pressure, taken up in dilute hydrochloric acid (2N, 150 mL) and extracted with diethyl ether (3×70 mL). The organic extracts were combined, washed with water (2×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (70 mL), and dried over magnesium sulfate, then adsorbed on silica and chromatographed on silica using a mobile phase of ethyl acetate/hexane. The major fraction was concentrated under reduced pressure to leave a colorless liquid. Yield 2.1 g (71 percent). 1H NMR (CDCl3) δ 7.49 (dt, J1=7.5 Hz, J2=1.2 Hz, 1H), 7.46 (br, 1H), 7.43 (dt, J1=7.8 Hz, J2=1.8 Hz, 1H), 7.39 (d, J=7.5 Hz, 1H), 7.33 (dt, J1=6.9 Hz, J2=2.1 Hz, 1H), 7.30 (dt, J1=7.2 Hz, J2=1.2 Hz, 1H), 7.25 (dt, J1=7.2 Hz, J2=1.5 Hz, 1H), 7.15 (dt, J1=6.9 Hz, J2=1.8 Hz, 2H), 4.01 (s, 2H); EI/MS 193 m/e (M+); CI/MS 194 m/e (M+1);

Workup

  1. temperaturewas refluxed under nitrogen for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with diethyl ether (3×70 mL)
  4. washwashed with water (2×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (70 mL)
  5. dry with materialdried over magnesium sulfate
  6. customchromatographed on silica using a mobile phase of ethyl acetate/hexane
  7. concentrationThe major fraction was concentrated under reduced pressure
  8. customto leave a colorless liquid

Sources & evidence

ORD record
ord-5b8db7a374c34a6482af0c3c645e89b0
Source dataset
uspto-grants-2009_01
Patent number
US07473669B2

Reaction notes

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