Bromine → 2-Bromo-4-ethylphenol

HRID 1453228Notes

Reaction equation

HRID 1453228 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 99.5%

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 (25 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 (42 g, 98%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3H), 2.58 (q, J=7.5 Hz, 2H), 5.36 (s, 1H), 6.93 (d, J=8.3 Hz, 1H), 7.03 (d, J=8.3 Hz, 1H), 7.28 (s, 1H).

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-856fde6ccb0f4217b8148ae7169d6b35
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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