Boron tribromide → HCID 135741338, compound

HRID 81017Notes

Reaction equation

HRID 81017 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[N:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[CH:16][CH:15]=2)[C:7]=1[C:8]#[N:9]>ClCCl.C(OCC)(=O)C>[Cl:5][C:6]1[N:13]=[CH:12][CH:11]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 73554558HCID 73554558, compound

Product 1

HCID 135741338HCID 135741338, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1.0 M dichloromethane solution of boron tribromide (12.26 mL, 12.26 mmol) was added to a solution of 2-chloro-4-(4-methoxyphenyl)nicotinonitrile (300 mg, 1.226 mmol) in dichloromethane (10 mL). The mixture was stirred at room temperature for 2 h, diluted with ethyl acetate (50 mL), and carefully quenched with saturated sodium bicarbonate (20 mL). The aqueous layer was separated and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with water (30 mL), brine (30 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 10-50% ethyl acetate in hexanes, gave 2-chloro-4-(4-hydroxyphenyl)nicotinonitrile as a brown solid (50 mg, 18% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.55 (1H, δ, J=5.22 Hz), 7.49-7.62 (2H, m), 7.38 (1H, δ, J=5.22 Hz), 6.94-7.05 (2H, m); MS (ES+) m/z: 231 (M+H); LC retention time: 2.841 min (analytical HPLC Method A).

Workup

  1. customcarefully quenched with saturated sodium bicarbonate (20 mL)
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined extracts were washed with water (30 mL), brine (30 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washSilica gel chromatography, eluting with 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8af209de9c1a4464b7142f91a14702d9
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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