Boron tribromide → HCID 67047765, compound

HRID 606843Notes

Reaction equation

HRID 606843 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1.C(=O)(O)[O-].[Na+]>ClCCl>[OH:6][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 67047572HCID 67047572, compound

Product 1

HCID 67047765HCID 67047765, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (1 mL, 1 mmol) dropwise to solution of 3-methoxy-5-phenylethynylpyridine, (prepared as described in EXAMPLE 30), (0.073 g, 0.35 mmol) in dichloromethane (0.7 mL) at −78° C. and stir for 15 min. Warm the reaction mixture to room temperature and stir overnight. Add a saturated aqueous solution of sodium bicarbonate to the reaction mixture and stir for 10 min to provide a biphasic solution. Separate the organic layer and wash it sequentially with a saturated solution of aqueous sodium bicarbonate and a saturated aqueous solution of sodium chloride. Dry (sodium sulfate), concentrate and purify by silica gel chromatography, eluting with 100:0 to 0:100 hexanes:ethyl acetate, to obtain the title compound (0.003 g, 4%).

Workup

  1. stirringstir overnight
  2. stirringstir for 10 min
  3. customto provide a biphasic solution
  4. customSeparate the organic layer
  5. washwash it sequentially with a saturated solution of aqueous sodium bicarbonate
  6. dry with materialDry (sodium sulfate)
  7. concentrationconcentrate
  8. custompurify by silica gel chromatography
  9. washeluting with 100:0 to 0:100 hexanes

Sources & evidence

ORD record
ord-e48e3f788a694bf88354f48ae8e78d2a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

Loading…