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

HRID 1750802Notes

Reaction equation

HRID 1750802 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-1433df31d9e3492aba8f9c6bac3ba614
Source dataset
uspto-grants-2015_10
Patent number
US09156860B2

Reaction notes

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