Boron tribromide → 4-(2,6-Dimethyl-4-nitro-phenoxy)-2-isopropyl-phenol

HRID 584004Notes

Reaction equation

HRID 584004 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:21]=1[O:22]C)[O:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=1[CH3:18])([CH3:3])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH3:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([CH3:14])[C:8]=1[O:7][C:6]1[CH:19]=[CH:20][C:21]([OH:22])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 103136024-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

Product 1

HCID 117796104-(2,6-Dimethyl-4-nitro-phenoxy)-2-isopropyl-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene (500 mg, 1.59 mmol) in CH2Cl2 (12 mL was added boron tribromide (1 M in CH2Cl2, 3.2 mL, 3.2 mmol). The resulting mixture was stirred 1 h at RT then quenched with water (15 mL) and 1 M HCL (10 mL). After stirring 30 min at RT, the solution was extracted with CH2Cl2 (3×20 mL). Combined extracts were washed with brine (50 ml), dried over anhydrous sodium sulfate, filtered, and concentrated to give the title compound of Step B. The title product of Step B was used in the next step without further purification. MS (APCl−) Calc.: 301. Found: 300.2 (M−1).

Workup

  1. customthen quenched with water (15 mL) and 1 M HCL (10 mL)
  2. stirringAfter stirring 30 min at RT
  3. extractionthe solution was extracted with CH2Cl2 (3×20 mL)
  4. washCombined extracts were washed with brine (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a77b3a6861ee43a1969877602bee0545
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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