Dimethylformamide → HCID 20749776, compound

HRID 499962Notes

Reaction equation

HRID 499962 reaction equation
CN(C=O)C.[Br:6]N1C(=O)CCC1=O.[C:14]1([C:20]2[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:23]=[CH:22][C:21]=2[OH:30])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[Br:6][C:22]1[CH:23]=[C:24]([C:26]([CH3:27])([CH3:29])[CH3:28])[CH:25]=[C:20]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:21]=1[OH:30]

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 113512-Biphenylol, 5-tert-butyl-HCID 67184N-bromobutanimide

Product 1

HCID 20749776HCID 20749776, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 20 mL DMF solution of N-bromosuccinimide (4.07 g, 22.9 mmol) was slowly added to a DMF solution (100 mL) of 2-phenyl-4-tert-butyl-phenol (4.93 g, 21.8 mmol), forming a dark green solution. After stirring in the dark for 48 h, the resultant dark red solution was poured into 500 mL of water, forming a cloudy solution. This was extracted with 95:5 hexane/toluene (3×200 mL), dried over MgSO4, filtered and the solvent removed to give 7 as a thick red oil. Yield: 6.32 g (95%).

Workup

  1. customforming a dark green solution
  2. customforming a cloudy solution
  3. extractionThis was extracted with 95:5 hexane/toluene (3×200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-31e5b086ffb047a68735d23631fb0791
Source dataset
uspto-grants-2010_08
Patent number
US07767773B2

Reaction notes

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