Dichloromethane → HCID 69991466, compound

HRID 1250118Notes

Reaction equation

HRID 1250118 reaction equation
B1(B2C3CCCC2CCC3)C2CCCC1CCC2.C12CCCC(CCC1)B12[H]B2(C3CCCC2CCC3)[H]1.[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH:43]=[CH2:44].ClCCl.[Br:49][C:50]1[CH:55]=[CH:54][CH:53]=[C:52](Br)[CH:51]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.[Pd](Cl)Cl.O.CN(C)C=O>[CH3:39][O:40][C:41](=[O:45])[CH2:42][CH2:43][CH2:44][C:52]1[CH:53]=[CH:54][CH:55]=[C:50]([Br:49])[CH:51]=1

Participants

10

Reactant 5

HCID 6344DichloromethaneHCID 79271,3-DibromobenzeneHCID 62657Potassium Phosphate, TribasicHCID 77314Methyl 3-butenoateHCID 113224419-Borabicyclo[3.3.1]nonane dimer

Product 1

HCID 69991466HCID 69991466, compoundYield 16%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

[9-Borabicyclo[3.3.1]nonane dimer] (13.4 mL, 6.68 mmol) (9-BBN dimer) was added to a solution of methyl-3-butenoate (0.71 mL, 6.68 mmol) in tetrahydrofuran (2.7 mL) at 0-5° C. under an argon atmosphere, and the mixture was stirred for 4 hours. N,N-Dimethylformamide (27 mL), palladium(II) chloride, dichloromethane (130 g, 0.16 mmol), 1,3-dibromobenzene (0.77 mL, 61.37 mmol) and potassium phosphate (powdered, 1.5 g, 6.94 mmol) were added. The mixture was treated at 50° C. overnight. Water was added and the mixture extracted with diethyl ether. The extract was washed with water, brine, and dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate) gave 4-(3-bromophenyl)butyric acid methyl ester as a clear oil (0.26 mg, 16%).

Workup

  1. additionThe mixture was treated at 50° C. overnight
  2. extractionthe mixture extracted with diethyl ether
  3. washThe extract was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customPurification by flash chromatography
  7. washeluting with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f2d14f1a6ab046f4bbd61fa0d584cbdd
Source dataset
uspto-grants-2002_01
Patent number
US06335459B1

Reaction notes

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