Hydrochloric Acid → 4-Bromo-2-(1-hydroxy-2-methylpropyl)phenol

HRID 1711788Notes

Reaction equation

HRID 1711788 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH:11]([Mg]Cl)([CH3:13])[CH3:12].[NH4+].[Cl-].Cl>CCOCC.C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]([OH:8])[CH:11]([CH3:13])[CH3:12])[CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 728635-BromosalicylaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 594578434-Bromo-2-(1-hydroxy-2-methylpropyl)phenolYield 122.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 5-bromo-2-hydroxybenzaldehyde (4.00 g, 19.9 mmol) in Et2O (40.0 mL) and THF (10.0 mL) was added dropwise to the isopropylmagnesium chloride (2 M in Et2O, 29.8 mL, 59.7 mmol) at ambient temperature. The reaction was stirred for about 15 min then MeOH (5 mL) was added followed by saturated aqueous NH4Cl and 1 N HCl. The reaction was extracted with EtOAc and then the combined organic layers were extracted with brine, dried over MgSO4, filtered, and evaporated to give the title compound as an oil (5.96 g, >100% yield). NMR showed some EtOAc but it was used as is the next step: 1H NMR (DMSO-d6, δ) 0.87 (3H, d), 1.03 (3H, d), 2.06 (1H, m), 2.77 (1H, s), 4.49 (1H, d), 6.78 (1H, d), 7.02 (1H, s), 7.25 (1H, dd), 8.11 (1H, s)

Workup

  1. extractionThe reaction was extracted with EtOAc
  2. extractionthe combined organic layers were extracted with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d14aeffb06304a61a898553ef856bca5
Source dataset
uspto-grants-2010_09
Patent number
US07790741B2

Reaction notes

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