Boron tribromide → HCID 178497536, compound

HRID 2356086Notes

Reaction equation

HRID 2356086 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 4674260Methyl 4-(6-methoxy-3-pyridinyl)benzoate

Product 1

HCID 178497536HCID 178497536, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of Example 252D (0.5 g, 2.2 mmol) in dichloromethane at −78° C. was treated with 1M BBr3 in dichloromethane (15 mL), warm to room temperature, and stirred for 18 hours. The reaction was quenched with methanol (5 mL), diluted with dichloromethane (100 mL), washed with water (30 mL), brine (30 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate to provide the desired product. MS (ESI) m/e 228, 230 (M−H)−, (M+H)+.

Workup

  1. customThe reaction was quenched with methanol (5 mL)
  2. additiondiluted with dichloromethane (100 mL)
  3. washwashed with water (30 mL), brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash column chromatography on silica gel with 2:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2d5167b405454628a346066bfb55a225
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…