Boron tribromide → HCID 67475118, compound

HRID 1293305Notes

Reaction equation

HRID 1293305 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH3:14])[CH:11]=[CH:12][N:13]=2)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:14][N:10]1[CH:11]=[CH:12][N:13]=[C:9]1[C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 39834387HCID 39834387, compound

Product 1

HCID 67475118HCID 67475118, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-(3-methoxyphenyl)-1-methyl-1H-imidazole (step 1, 724 mg, 3.8 mmol) in dichloromethane (2 mL) was added a solution of boron tribromide (1 M in dichloromethane, 5 mL) at 0° C. The mixture was stirred at 0° C. for 3 h and at room temperature for 40 h. The mixture was poured into aqueous sodium bicarbonate solution (10 mL). The precipitated solids were collected by filtration and dried under reduced pressure to afford 205 mg (31%) of the title compound as a pale brown solid: 1H-NMR (CDCl3) δ 7.29–7.22 (2H, m), 7.09–7.07 (2H, m), 6.94 (1H, d, J=1.1 Hz), 6.83–6.78 (1H, m), 3.72 (3H, s); MS (ESI) m/z 175 (M+H)+, 173 (M−H)−.

Workup

  1. filtrationThe precipitated solids were collected by filtration
  2. customdried under reduced pressure

Sources & evidence

ORD record
ord-a4e99ed489f548b183f7b4e79de539e1
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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