Boron tribromide → HCID 12465308, compound

HRID 1866531Notes

Reaction equation

HRID 1866531 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH3:16]>ClCCl.C(=O)([O-])O.[Na+]>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH3:16]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 1447294-Methoxy-3-methylphenylacetonitrile

Product 1

HCID 12465308HCID 12465308, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-78 °C

Procedure

Boron tribromide (1M in dichloromethane, 6.2 mL, 6.2 mmol) was added to a solution of 4-methoxy-3-methylphenylacetonitrile (0.2 g, 1.24 mmol) in dichloromethane (10 mL), cooled to −78° C. The reaction mixture was stirred at this temperature for 1 hour and then at room temperature for 2 hours. The mixture was then re-cooled to −78° C., diluted with sodium hydrogen carbonate solution and allowed to warm to room temperature. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound as a white solid in 87% yield, 0.16 g. 1H NMR (400 MHz, CDCl3) δ:7.07 (1H, s), 7.00 (1H, d), 6.76 (1H, d), 3.65 (2H, s), 2.25 (3H, s) ppm; LRMS APCI m/z 146 [M−H]−.

Workup

  1. waitat room temperature for 2 hours
  2. temperatureThe mixture was then re-cooled to −78° C.
  3. temperatureto warm to room temperature
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afb0a376ced84238add2ef653887b964
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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