Diethyl Ether → 3-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehyde

HRID 2377468Notes

Reaction equation

HRID 2377468 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1.[CH2:14]([O:16]CC)C>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:7]([CH3:8])=[C:6]([C:5]([OH:9])=[C:4]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1)[CH:14]=[O:16]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol2×

Product 1

HCID 211071503-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzaldehydeYield 61%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred, cooled (ice bath) solution of 4-bromo-2-tert-butyl-5-methyl-phenol (Intermediate 139, 0.85 g, 3.5 mmol) in anhydrous dichloromethane (7 mL) was treated with titanium tetrachloride (0.64 mL, 5.8 mmol) followed by □□-dichloro methyl ether (0.3 g, 3.5 mmol). The reaction mixture was allowed to warm to ambient temperature for 4 h. The reaction mixture was diluted with diethyl ether, washed with brine (×1) and dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was subjected to flash column chromatography over silica gel (230-400 mesh) using 1% ethyl acetate in hexane to afford the title compound as a yellow solid (0.58 g, 61%).

Workup

  1. washwashed with brine (×1)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo to a residue which

Sources & evidence

ORD record
ord-852714f2a12b4ff8b58eef7c21e490ae
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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