Acrylic Acid → HCID 59443450, compound

HRID 1035586Notes

Reaction equation

HRID 1035586 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1.[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C(C)=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Br:10][C:4]1[CH:3]=[C:2](/[CH:13]=[CH:12]/[C:11]([OH:15])=[O:14])[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Participants

9

Reactant 5

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 110218123,5-Dibromoanisole

Product 1

HCID 59443450HCID 59443450, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole %, 20.66 mg), triphenylphosphine (4 mole %, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32% (751 mg).

Workup

  1. stirringthe mixture was stirred at 100° C. for some minutes
  2. customThe aqueous phase was subsequently separated
  3. customThe precipitate that formed
  4. customwas dried
  5. custompurified by means of column chromatography (eluent hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-813684a0a6e24e379344dc472c2a5d94
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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