Ethyl Acetate → HCID 67065969, compound

HRID 2093135Notes

Reaction equation

HRID 2093135 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[Cl:12].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>O.CCO.C1(C)C=CC=CC=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.CCCCCC>[Cl:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 39058267HCID 39058267, compound

Product 1

HCID 67065969HCID 67065969, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8058HexaneSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of methyl 4-iodo-3-chlorobenzoate (1.20 g, 4.05 mmol) from Step A, 4-methoxy phenyl boronic acid (1.23 g, 8.1 mmol), tetrakis(triphenylphosphine)palladium (0.23 g, 5% mol) and sodium carbonate (0.94 g, 8.9 mmol) in 50 ml of water/EtOH/toluene (1:2:4) was heated to reflux overnight. TLC (EtOAc:hexane/1:9) showed that the reaction was over. The solvents were removed. Water (30 ml) was added. The organic was extracted with methylene chloride (3×50 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after flash column using EtOAc:hexane/1:9 as the eluant. 1H NMR (CDCl3, 500 MHz): δ 8.16 (d, J=1.5 Hz, 1H), 7.97 (dd, J=8, 1.5 Hz, 1H), 7.43 (m, 3H), 7.01 (d, J=6.5 Hz, 2H), 4.00 (s, 3H), 3.91 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe solvents were removed
  4. additionWater (30 ml) was added
  5. extractionThe organic was extracted with methylene chloride (3×50 ml)
  6. washThe combined methylene chloride layers were washed with brine
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-05e6743d9bf94606838fc41e7ffc32ec
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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