Toluene → 4-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-(1-hydroxyethyl)-6-isopropylphenol

HRID 1392557Notes

Reaction equation

HRID 1392557 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].[CH3:26][Al](C)C.C1(C)C=CC=CC=1>C(Cl)Cl>[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]([CH3:15])[CH3:16])[C:8]([OH:13])=[C:9]([CH:10]([OH:11])[CH3:26])[CH:12]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 16682925TrimethylaluminumHCID 596784105-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde

Product 1

HCID 596784354-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-(1-hydroxyethyl)-6-isopropylphenolYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

5-(2,6-Dibromo-3-methyl-4-nitrophenoxy)-2-hydroxy-3-isopropylbenzaldehyde of Part 8D (210 mg, 0.44 mmol) was dissolved in CH2Cl2 (5 mL) and cooled to 4° C. Me3Al in toluene (0.355 mL, 0.67 mmol, 2N) was added to the mixture and the reaction was stirred for 16 hours at room temperature. The reaction mixture was quenched with ice water and extracted with EtOAc. The organic phase was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Filtration through a pad of silica gave 195 mg (93%) of 4-(2,6-dibromo-3-methyl-4-nitrophenoxy)-2-(1-hydroxyethyl)-6-isopropylphenol as a light yellow solid.

Workup

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. filtrationFiltration through a pad of silica

Sources & evidence

ORD record
ord-ddeffb0d9a674ffd9656b952f43117ac
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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