Boron tribromide → HCID 178497536, compound

HRID 1785813Notes

Reaction equation

HRID 1785813 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-e6ea4689622b4c68ba2a6654d4f4890d
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

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