Water → 4'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrile

HRID 1064746

Reaction equation

HRID 1064746 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 25134Boron tribromideHCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

Product 1

HCID 136359914'-Hydroxy-3-methyl-1,1'-biphenyl-4-carbonitrileYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 106A (5.60 g, 25.4 mmol) in CH2Cl2 (120 mL) at 78° C. was treated with 1.0 M BBr3 (in CH2Cl2, 76 mL, 76.0 mmol) dropwise over 1 hour. After stirring for 14 hours at room temperature, the mixture was warmed to 0° C. (ice bath) and treated with water (0.5 mL). After 10 minutes, additional water was added (2.0 mL), ice bath was removed, and 5.0 mL of water was added. The mixture was then treated with another 20 mL of water and allowed to stir for 45 minutes. The mixture was filtered and the filtrate extracted with CH2Cl2. The CH2Cl2 layers were combined, dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound as an off-white powder (5.04 g, 94% yield). 1HNMR (300 MHz, CDCl3) δ 2.35 (s, 3H), 5.0 (s, 1H), 6.79-7.50 (m, 7H); MS (DCI) m/z 210 (M+H)+.

Workup

  1. temperaturethe mixture was warmed to 0° C. (ice bath)
  2. waitAfter 10 minutes
  3. customwas removed
  4. addition5.0 mL of water was added
  5. additionThe mixture was then treated with another 20 mL of water
  6. stirringto stir for 45 minutes
  7. filtrationThe mixture was filtered
  8. extractionthe filtrate extracted with CH2Cl2
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-74aebf7432a44d20ac034b3d7391bcc7
Source dataset
uspto-grants-2005_11
Patent number
US06969730B2

Linked notes

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