Methanol → 2-Bromo-5-tert-butylphenol

HRID 1468480Notes

Reaction equation

HRID 1468480 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[C:55]([C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=1O)([CH3:58])([CH3:57])[CH3:56].C[OH:67]>C(Cl)Cl>[Br:1][C:62]1[CH:63]=[CH:64][C:59]([C:55]([CH3:58])([CH3:57])[CH3:56])=[CH:60][C:61]=1[OH:67]

Participants

5

Reactant 3

HCID 887MethanolHCID 69232-Tert-ButylphenolHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 123362182-Bromo-5-tert-butylphenolYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve tetrabutylammonium tribromide (48.1 g, 100 mmol) and 2-tert-butylphenol (15 g, 100 mmol) in CH2Cl2(180 mL) and MeOH (120 mL) at 0° C., and stir overnight. Evaporate the solvent, and partition residue between Et2O (150 mL×3) and water (200 mL). Combine organic layers, and wash with 1M HCl (aqueous, 200 mL) and brine (100 mL), dry over MgSO4, filter, and rotary evaporate to give 23 g (100%) of 2-bromo-5-(1,1-dimethylethyl)phenol as a yellowish oil. 1H NMR (400 MHz, CDCl3) δ 7.39 (d, J=8.5 Hz, 1H), 7.09 (d, J=2.3 Hz, 1H), 6.87 (dd, J=8.5, 2.3 Hz, 1H), 5.57 (s, 1H), 1.31 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 153.15, 151.81, 131.37, 119.22, 113.48, 106.88, 34.68, 31.20.

Workup

  1. customEvaporate the solvent
  2. custompartition residue between Et2O (150 mL×3) and water (200 mL)
  3. washCombine organic layers, and wash with 1M HCl (aqueous, 200 mL) and brine (100 mL)
  4. dry with materialdry over MgSO4
  5. filtrationfilter
  6. customrotary evaporate

Sources & evidence

ORD record
ord-9a4258f74fed47f78263250fee5e24fc
Source dataset
uspto-grants-2015_04
Patent number
US09000108B2

Reaction notes

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