Water → 2,4-Bis(tert-butyl)-6-[[(2,6-dibromophenyl)amino]methyl]phenol

HRID 601092Notes

Reaction equation

HRID 601092 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH:15]=[N:16][C:17]2[C:22]([Br:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Br:24])[C:6]=1[OH:25])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>CO>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([CH2:15][NH:16][C:17]2[C:22]([Br:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Br:24])[C:6]=1[OH:25])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 1363467102,4-Bis(tert-butyl)-6-[[(2,6-dibromophenyl)imino]methyl]phenol

Product 1

HCID 866276672,4-Bis(tert-butyl)-6-[[(2,6-dibromophenyl)amino]methyl]phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2,4-bis(tert-butyl)-6-[[(2,6-dibromophenyl)imino]methyl]phenol (0.91 g, 2.41 mmol) in methanol (20 ml) was added NaBH4 (1.2 g), in small portions. The yellow suspension was stirred for 2 hours during which the yellow solution turned clear. Water (10 ml) was then slowly added, the organic phase separated and the aqueous phase extracted with dichloromethane (3×10 ml). The organic fractions were combined, dried (NaSO4), and the solvent removed under reduced pressure. The crude product was purified by recrystallisation from hot hexane to afford the product as large colourless crystals. Yield 0.48 g, 95%.

Workup

  1. customthe organic phase separated
  2. extractionthe aqueous phase extracted with dichloromethane (3×10 ml)
  3. dry with materialdried (NaSO4)
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was purified by recrystallisation from hot hexane

Sources & evidence

ORD record
ord-58d0005d99bf4b80a0e98e4d6564161a
Source dataset
uspto-grants-2011_03
Patent number
US07902308B2

Reaction notes

Loading…