Boron tribromide → 4-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylphenol

HRID 393393Notes

Reaction equation

HRID 393393 reaction equation
[Br:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Br:23])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11]C)=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:6]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[C:16]([Br:23])[C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([CH:13]([CH3:15])[CH3:14])[CH:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117442094-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylanisole

Product 1

HCID 226603024-(2,6-Dibromo-4-nitrophenoxy)-2-isopropylphenolYield 110%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
8.699999809265137 °C

Procedure

A 12 L three-necked round bottom flask equipped with a mechanical stirrer, an addition funnel, and a temperature probe was charged with 4-(2,6-dibromo-4-nitrophenoxy)-2-isopropylanisole (752.1 g, 1.69 moles), which was dissolved by stirring in dichloromethane (2 L) at room temperature. The mixture was cooled to 8.7° C. in an ice-water bath. A solution of boron tribromide (2.050 L, 1M in CH2Cl2, 2.05 moles) was added over 30 min. An increase of approximately 10° C. in the temperature of the reaction mixture was observed. The ice-water bath was removed and the reaction mixture was allowed to stir at room temperature until the reaction was complete, as assayed by HPLC. The reaction mixture was cooled once more in an ice-water bath, then quenched by slow addition of methanol (850 mL), during which the temperature of the reaction mixture was maintained below 18° C. Saturated aqueous sodium bicarbonate solution was added until the pH of the reaction mixture was 6 or 7. The aqueous phase was separated and washed with aliquots of ethyl acetate (2×1 L). The organic layers were combined and the solvent removed under a vacuum at room temperature to yield crude 4-(2,6-dibromo-4-nitrophenoxy)-2-isopropylphenol (796 g, 110%).

Workup

  1. customA 12 L three-necked round bottom flask equipped with a mechanical stirrer, an addition funnel
  2. dissolutionwas dissolved
  3. temperatureAn increase of approximately 10° C. in the temperature of the reaction mixture
  4. customThe ice-water bath was removed
  5. temperatureThe reaction mixture was cooled once more in an ice-water bath
  6. customquenched by slow addition of methanol (850 mL), during which the temperature of the reaction mixture
  7. temperaturewas maintained below 18° C
  8. additionSaturated aqueous sodium bicarbonate solution was added until the pH of the reaction mixture
  9. customThe aqueous phase was separated
  10. washwashed with aliquots of ethyl acetate (2×1 L)
  11. customthe solvent removed under a vacuum at room temperature

Sources & evidence

ORD record
ord-6049a1fcff494be6acfd5e7ce2d97269
Source dataset
uspto-grants-2004_10
Patent number
US06806381B2

Reaction notes

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