Water → HCID 21200954, compound

HRID 363051Notes

Reaction equation

HRID 363051 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]#[N:15])=[CH:16][CH:17]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 44129571HCID 44129571, compound

Product 1

HCID 21200954HCID 21200954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 26-3 (0.391 g, 1.75 mmol) in methylene chloride (6 ml) cooled in an ice-bath in a 3-necked round bottom flask equipped with a nitrogen inlet and rubber septum was added 1.0M boron tribromide in methylene chloride (3.9 ml, 3.9 mmol) via syringe. The resulting mixture was stirred 18 h while warming to ambient temperature. Water (7 ml) was added and the mixture was extracted with ether (35 ml). The organic fraction was washed with brine (10 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:5 increasing to 1:3), to give product 26-4 as a white solid, mp: 163°-164° C.

Workup

  1. customequipped with a nitrogen inlet
  2. extractionthe mixture was extracted with ether (35 ml)
  3. washThe organic fraction was washed with brine (10 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with ethyl acetate/hexane (1:5 increasing to 1:3)

Sources & evidence

ORD record
ord-0942628a91f448e199247feee0023e0b
Source dataset
uspto-grants-1999_02
Patent number
US05872138

Reaction notes

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