Hydrogen Bromide → 4-(2-Bromoethyl)phenol

HRID 133776

Reaction equation

HRID 133776 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7]O)=[CH:4][CH:3]=1.[BrH:11]>O>[Br:11][CH2:7][CH2:6][C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 10393Tyrosol

Product 1

HCID 842214-(2-Bromoethyl)phenolYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(4-Hydroxyphenethyl) alcohol (1.50 g, 0.01086 mol) and 48 wt. % hydrobromic acid (10 ml) were heated at 100° C. for 1.5 h. After being cooled, the reaction mixture was poured into water and extracted with ethyl acetate. The extracts were washed with water, dried and concentrated in vacuo to give a raw product. Purification by flash chromatography (heptane/ethyl acetate 9:1) gave a pure product (2.01 g, 92%). 1H NMR (400 MHz, DMSO-d6): 2.99 (2H, t, 3J=7.4 Hz), 3.63 (2H, t, 3J=7.4 Hz), 6.68 (2H, d, 3J=8.5 Hz), 7.05 (2H, d, 3J=8.3 Hz), 9.24 (1H, s, —OH).

Workup

  1. temperatureAfter being cooled
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give a raw product
  7. customPurification by flash chromatography (heptane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-9609a09fd22149698b73eed8b1367578
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Linked notes

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