1,2-Dimethoxyethane → HCID 54217329, compound

HRID 2421627Notes

Reaction equation

HRID 2421627 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:12]=[CH:13][C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH2:15]1.C([O-])([O-])=O.[Na+].[Na+].COCCOC>O.C1(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)C=CC=CC=1>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:9]=[CH:10][CH:11]=[C:2]([CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 67214057HCID 67214057, compound

Product 1

HCID 54217329HCID 54217329, compound

Reagents, catalysts & solvents 2

HCID 178420554HCID 178420554, compoundCatalystHCID 962WaterSolvent2×

Procedure

Methyl 3-bromobenzoate (458 mg, 2 mmol), 1-styreneboronic acid pinacoyl ester (484 mg, 2.1 mmol), Na2CO3 (222 mg, 2.1 mmol), tetrakis(triphenylphosphino)palladium (116 mg, 0.1 mmol), water (4 mL) and 1,2-dimethoxyethane (6 mL) were stirred with reflux conditions for one hour, under nitrogen. The reaction mixture was diluted with water and was extracted three times with EtOAc. The organic layers were combined, washed with water and then brine, dried over MgSO4 and concentrated. The product was purified by trituration with Et2O. White crystals were obtained (393 mg, 82%). NMR 1H (ppm, CDCl3): 8.19 (t, J4=1.6 Hz, 1H), 7.91 (dt, J3=7.7 Hz, J4=1.3 Hz, 1H), 7.67 (d, J3=7.8 Hz, 1H), 7.52 (d, J3=7.3 Hz, 2H), 7.42 (t, J3=7.9 Hz, 1H), 7.36 (t, J3=7.4 Hz, 2H), 7.30-7.26 (m, 1H), 7.19 (d, J3=16.3 Hz, 1H), 7.11 (d, J3=16.4 Hz, 1H), 3.06 (s, 3H).

Workup

  1. extractionwas extracted three times with EtOAc
  2. washwashed with water
  3. dry with materialbrine, dried over MgSO4
  4. concentrationconcentrated
  5. customThe product was purified by trituration with Et2O
  6. customWhite crystals were obtained (393 mg, 82%)

Sources & evidence

ORD record
ord-2a7b4def46c2476fbd538e9e13664739
Source dataset
uspto-grants-2011_06
Patent number
US07956216B2

Reaction notes

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