Boron tribromide → HCID 22669999, compound

HRID 1595692Notes

Reaction equation

HRID 1595692 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=3)=[CH:11][CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:14]=2)=[CH:5][CH:4]=1.BrB(Br)Br>ClCCl.C([O-])(=O)C.[Na+]>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([C:19]3[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=3)=[CH:11][CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 14570137HCID 14570137, compound

Product 1

HCID 22669999HCID 22669999, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 517045Sodium AcetateSolvent

Procedure

2.7 g of methyl 4,4″-dimethoxy-(1,1′:2′,1″-terphenyl)-5′-carboxylate (product prepared according to J. Med. Chem. (1989) 32 1814-1820) in 30 ml of dichloromethane is cooled down to −30° C., under an inert atmosphere, 2.7 ml of tribromoborane is added and agitation is carried out at −30° C. for 16 hours. The reaction medium is diluted with a saturated solution of sodium acetate, the aqueous phase is extracted with ethyl acetate, the organic phase is dried then evaporated. The crude reaction product is chromatographed on silica eluting with a cyclohexane/ethyl acetate mixture 70/30. In this way 814 mg of expected product is obtained.

Workup

  1. additionis added
  2. extractionthe aqueous phase is extracted with ethyl acetate
  3. customthe organic phase is dried
  4. customthen evaporated
  5. customThe crude reaction product
  6. customis chromatographed on silica eluting with a cyclohexane/ethyl acetate mixture 70/30

Sources & evidence

ORD record
ord-2d754a62b2f44ffa8df1e7441ca58b58
Source dataset
uspto-grants-2001_09
Patent number
US06288126B1

Reaction notes

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