Boron tribromide → HCID 21107085, compound

HRID 1765399Notes

Reaction equation

HRID 1765399 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:13])C(I)=C[O:11][C:6]=2[CH:5]=[C:4]([O:14][CH2:15]OCC[Si](C)(C)C)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[CH:5]=[C:6]([OH:11])[C:7]=1[CH:8]=[O:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21107093HCID 21107093, compound

Product 1

HCID 21107085HCID 21107085, compoundYield 219.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-chloro-4,6-dimethoxybenzaldehyde [4] (3.15 g) in dichloromethane (30 mL) cooled at −78° C. was added boron tribromide (1M solution in dichloromethane, 16 mL). The mixture was stirred at −78° C. for 30 min, warmed and stirred at room temperature for 18 h. The mixture was cooled to 0° C., poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent gave the title compound (2.85 g). 1H NMR (DMSO-d6): 12.15 (s, 1H), 10.14 (s, 1H), 6.74 (d, 1H, J=2.1 Hz), 6.53 (d, 1H, J=2.1 Hz), 3.86 (s, 3H).

Workup

  1. temperaturewarmed
  2. stirringstirred at room temperature for 18 h
  3. temperatureThe mixture was cooled to 0° C.
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-7ebc30303bc243b7b7badee8b6f63dd5
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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