Bromine → 2-Bromo-4-ethylphenol

HRID 858774Notes

Reaction equation

HRID 858774 reaction equation
[Br:1]Br.[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)[CH3:4]>C(Cl)Cl>[Br:1][C:7]1[CH:6]=[C:5]([CH2:3][CH3:4])[CH:10]=[CH:9][C:8]=1[OH:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 312424-Ethylphenol

Product 1

HCID 166412522-Bromo-4-ethylphenolYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (11.6 mL, 0.23 mol) was added slowly to a cooled 0° C. of 4-ethylphenol (2 g, 0.21 mol) dissolved in CH2Cl2 (125 mL). After the addition was complete the reaction mixture was stirred for 5 mins and then quenched with 1N NaOH. The reaction mixture was diluted with H2O and the layers separated. The organic layer was concentrated to an orange oil. Purification by flash column chromatography (0% to 5% EtOAc in hexanes) gave the title compound as a clear oil (4 g, 98%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3 H), 2.58 (q, J=7.5 Hz, 2 H), 5.36 (s, 1 H), 6.93 (d, J=8.3 Hz, 1 H), 7.03 (d, J=8.3 Hz, 1 H), 7.28 (s, 1 H).

Workup

  1. additionAfter the addition
  2. customquenched with 1N NaOH
  3. additionThe reaction mixture was diluted with H2O
  4. customthe layers separated
  5. concentrationThe organic layer was concentrated to an orange oil
  6. customPurification by flash column chromatography (0% to 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2daa4e60d2f945519ce3be79734f518e
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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