Potassium Carbonate → HCID 58999564, compound

HRID 1877913Notes

Reaction equation

HRID 1877913 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[C:15]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>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.CN(C=O)C>[CH3:15][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 66885844HCID 66885844, compound

Product 1

HCID 58999564HCID 58999564, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-bromo-3-trifluoromethoxybenzonitrile (10.0 g, 37.6 mmol), K2CO3 (15.6 g, 113 mmol), trimethylboroxine (5.5 mL, 39.5 mmol) and DMF (150 mL) is degassed for 10 min with nitrogen before Pd(PPh3)4 (4.34 g, 3.76 mmol) is added. The mixture is then sealed and heated to 120° C. for 14 h. The mixture is then concentrated and then partitioned between Et2O and 50% brine solution. The aqueous phase is further extracted with Et2O and the combined organic layers are dried (Na2SO4) and concentrated. The residue is purified via flash chromatography (10% EtOAc/hexanes) to give 4-methyl-3-trifluoromethoxybenzonitrile. H NMR (400 MHz, CDCl3) δ (ppm) 2.40 (s, 3H), 7.40 (d, J=7.7 Hz, 1H), 7.50 (s, 1H), 7.51 (dd, J=7.7, 1.5 Hz, 1H). MS (ESI) m/z 202.1.

Workup

  1. additionis added
  2. customThe mixture is then sealed
  3. concentrationThe mixture is then concentrated
  4. custompartitioned between Et2O and 50% brine solution
  5. extractionThe aqueous phase is further extracted with Et2O
  6. dry with materialthe combined organic layers are dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is purified via flash chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-41f4111493834468a1e8b8fac21ca075
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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