Boron tribromide → Phenol, 5-chloro-2-nitro-

HRID 440650

Reaction equation

HRID 440650 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([O:12]C)[CH:11]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N+:14]([O-:16])=[O:15])=[C:10]([OH:12])[CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 811105-Chloro-2-nitroanisole

Product 1

HCID 11900Phenol, 5-chloro-2-nitro-Yield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in methylene chloride (400 mL, 0.40 mole) was cooled to -20° C. A solution of 37.5 g (0.20 mole) of 5-chloro-2-nitroanisole in 200 mL of methylene chloride was added slowly to the first solution. Upon completion of addition, the mixture was allowed to warm to ambient temperature at which it stirred for about 16 hours. At the conclusion of this period the reaction mixture was poured into ice water. The organic layer was separated from the aqueous layer and was evaporated under reduced pressure, leaving 31.40 g of 5-chloro-2-nitrophenol as a solid residue, m.p. 38°-39° C.

Workup

  1. additionUpon completion of addition
  2. customThe organic layer was separated from the aqueous layer
  3. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-37fa2d71589d41f490cc9af9baa1e593
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Linked notes

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