Boron tribromide → 3-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenol

HRID 537453Notes

Reaction equation

HRID 537453 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]2)=[C:5]([CH3:18])[CH:4]=1.B(Br)(Br)Br>ClCCl>[CH3:18][C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][C:6]=1[N:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 681566421-(4-methoxy-2-methylphenyl)-4-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 653137983-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenolYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 1-(4-methoxy-2-methylphenyl)-4-(trifluoromethyl)-1H-pyrazole (400 mg, 2 mmol) in dichloromethane (5 mL) was added boron tribromide (1 g, 6 mmol). The mixture was allowed to warm to room temperature and stir overnight. The reaction was quenched with methanol (2 mL), diluted with water (10 mL), and extracted with dichloromethane (3×10 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated to give 3-methyl-4-(4-(trifluoromethyl)-1H-pyrazol-1-yl)phenol (390 mg, 99%) as a brown solid. 1H NMR (400 MHz, CDCl3, δ): 7.83 (s, 1H), 7.74 (s, 1H), 7.08 (d, J=8.4 Hz, 1H), 6.65 (s, 1H), 6.62 (d, J=8.4 Hz, 1H), 5.57 (s, 1H), 2.05 (s, 3H).

Workup

  1. customThe reaction was quenched with methanol (2 mL)
  2. additiondiluted with water (10 mL)
  3. extractionextracted with dichloromethane (3×10 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-368c813a2e3546e2836653544f263d48
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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