2,6-Dichlorophenol → 4-Bromo-2,6-dichlorophenol

HRID 532182Notes

Reaction equation

HRID 532182 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[OH:9].[Br:10]Br.S([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[Br:10][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([OH:9])=[C:4]([Cl:8])[CH:5]=1

Participants

5

Reactant 3

HCID 68992,6-DichlorophenolHCID 24408BromineHCID 24437Sodium Sulfite

Product 1

HCID 185874-Bromo-2,6-dichlorophenolYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 2,6-dichlorophenol (20 g, 123.4 mmol) in acetonitrile (200 mL) was cooled to 0° C. and bromine (23.7 g) in acetonitrile (50 mL) was added dropwise. The red solution was stirred at 0° C. for 2 h and a saturated aqueous solution of sodium sulphite was added until the red color disappeared. The phases were separated and the aqueous phase was extracted three times with ethyl acetate. Concentration of the combined organic phases gave a yellow oil, which was purified on a silica gel column (heptane/ethyl acetate, 10:1) to give 17.8 g of 4-bromo-2,6-dichlorophenol as a white solid. Yield: 60%; 1H NMR (400 MHz, CDCl3): δ 7.42 (s, 2H), 5.9 (br s, 1H) ppm.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted three times with ethyl acetate
  3. customConcentration of the combined organic phases gave a yellow oil, which
  4. customwas purified on a silica gel column (heptane/ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-f5d1c2e412a14d83b92628e3979d2f63
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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