Boron tribromide → 3-Bromo-2,5-dichlorophenol

HRID 505545Notes

Reaction equation

HRID 505545 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([O:13]C)[C:7]=1[Cl:15]>ClCCl.O>[Br:5][C:6]1[C:7]([Cl:15])=[C:8]([OH:13])[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 577991361-Bromo-2,5-dichloro-3-methoxybenzene

Product 1

HCID 684280893-Bromo-2,5-dichlorophenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide as a 1 M solution in dichloromethane (41 mL, 41 mmol) was added to 1-bromo-2,5-dichloro-3-methoxybenzene (10.5 g, 41 mmol) in dichloromethane (100 mL) at −78° C. under N2. The reaction mixture was allowed to warm to room temperature, and after 21 hours, the mixture was poured into 100 g of ice, diluted with 100 g of water, and the organic layer separated. The aqueous layer was extracted with dichloromethane (200 mL) and the combined organic extracts were dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. 1H NMR (CDCl3) δ 7.20 (m, 1H), 7.00 (m, 1H), 5.70 (s, 1H).

Workup

  1. customthe organic layer separated
  2. extractionThe aqueous layer was extracted with dichloromethane (200 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2b076eeb0e9a42aca9b912429a2b1b5f
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

Loading…