Boron tribromide → HCID 178497536, compound

HRID 2085753Notes

Reaction equation

HRID 2085753 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-567b9eaeb62c48ceaac794b68f157b34
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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