Boron tribromide → HCID 9814584, compound

HRID 412851Notes

Reaction equation

HRID 412851 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](OC)=[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:8]=[CH:7][C:6]([C:9]2[C:10]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)=[CH:11][CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 14570137HCID 14570137, compound

Product 1

HCID 9814584HCID 9814584, compoundYield 35.9%

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

Sources & evidence

ORD record
ord-80190a031b884100ac6f3210ce7995d5
Source dataset
uspto-grants-2003_05
Patent number
US06563008B2

Reaction notes

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