Sodium borohydride → 4-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxymethyl-6-isopropylphenol

HRID 1392559Notes

Reaction equation

HRID 1392559 reaction equation
[Br:1][C:2]1[C:20]([CH3:21])=[C:19]([N+:22]([O-:24])=[O:23])[CH:18]=[C:17]([Br:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11].[BH4-].[Na+]>CCO.C1COCC1>[Br:1][C:2]1[C:20]([CH3:21])=[C:19]([N+:22]([O-:24])=[O:23])[CH:18]=[C:17]([Br:25])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8]([OH:13])=[C:9]([CH2:10][OH:11])[CH:12]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 596784105-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde

Product 1

HCID 596784304-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxymethyl-6-isopropylphenolYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde of Part 8D (100 mg, 0.21 mmol) and NaBH4 (9.0 mg, 0.23 mmol) was dissolved in a mixture of EtOH and THF (3 mL, 2:1) at room temperature. After 1.5 hours of stirring at room temperature, the reaction mixture was concentrated and the residue suspended in CHCl3. The suspension was washed with 1N HCl and the two phases were separated with a phase separator (IST) before concentration of the organic phase. The residue was purified on column (silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 7:3) to give 85 mg (85%) of 4-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-hydroxymethyl-6-isopropylphenol as a light yellow foam.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. washThe suspension was washed with 1N HCl
  3. customthe two phases were separated with a phase separator (IST) before concentration of the organic phase
  4. customThe residue was purified on column (silica gel, gradient elution: n-heptane/EtOAc from 1:0 to 7:3)

Sources & evidence

ORD record
ord-5cd612c4dd854104a9215590bb42f95e
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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