Sodium borohydride → 2,4-Bis(tert-butyl)-6-[[(2,6-dichlorophenyl)amino]methyl]-phenol

HRID 601094Notes

Reaction equation

HRID 601094 reaction equation
C(C1C=C(C(C)(C)C)C=C(CNC2C(Br)=CC=CC=2Br)C=1O)(C)(C)C.[BH4-].[Na+].[C:28]([C:32]1[CH:37]=[C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=[C:34]([CH:42]=[N:43][C:44]2[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:45]=2[Cl:51])[C:33]=1[OH:52])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([C:32]1[CH:37]=[C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:35]=[C:34]([CH2:42][NH:43][C:44]2[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:45]=2[Cl:51])[C:33]=1[OH:52])([CH3:29])([CH3:30])[CH3:31]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 866276672,4-Bis(tert-butyl)-6-[[(2,6-dibromophenyl)amino]methyl]phenolHCID 1363467092,4-Bis(tert-butyl)-6-[[(2,6-dichlorophenyl)imino]methyl]phenol

Product 1

HCID 866276662,4-Bis(tert-butyl)-6-[[(2,6-dichlorophenyl)amino]methyl]-phenol

Procedure

Using an analogous procedure to the synthesis of 2,4-bis(tert-butyl)-6-[[(2,6-dibromophenyl)amino]methyl]phenol described above, NaBH4 (0.8 g) was added to a solution of 2,4-bis(tert-butyl)-6-[[(2,6-dichlorophenyl)imino]methyl]phenol (0.91 g, 2.41 mmol). The product was purified from hot hexane and isolated as colourless crystals. Yield 0.61 g, 67%.

Workup

  1. customThe product was purified from hot hexane
  2. customisolated as colourless crystals

Sources & evidence

ORD record
ord-ee8661360f144b058500a09e18e60a14
Source dataset
uspto-grants-2011_03
Patent number
US07902308B2

Reaction notes

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