3-Chlorophenol → 1-(4-Bromobutoxy)-3-chlorobenzene

HRID 1160493Notes

Reaction equation

HRID 1160493 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15]Br.[Na+].[Br-]>O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][O:8][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 253881Sodium Bromide

Product 1

HCID 27349111-(4-Bromobutoxy)-3-chlorobenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A 1 L flask provided with a stirrer was charged with 128.6 g (1.0 mol) of m-chlorophenol (available from Tokyo Chemical Industry Co., Ltd.), 52.0 g (1.3 mols) of sodium hydroxide (available from Wako Pure Chemical Industries Ltd.), 259.1 g (1.2 mols) of 1,4-dibromobutane (available from Tokyo Chemical Industry Co., Ltd.) and 300 g of water. The content was maintained at 80° C. for 4 hours. Then the reaction liquid was cooled to room temperature, and deposited NaBr, produced by side reaction, was filtered off. The organic phase was separated and subjected to distillation under reduced pressure to give 216.9 g of the target m-(4-bromobutoxy)chlorobenzene (yield: 79%, purity: 96%).

Workup

  1. customA 1 L flask provided with a stirrer
  2. customThen the reaction liquid
  3. temperaturewas cooled to room temperature
  4. customproduced by side reaction
  5. filtrationwas filtered off
  6. customThe organic phase was separated
  7. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-f4b0c2cc67ad4706991672aedb23bf6e
Source dataset
uspto-grants-2010_10
Patent number
US07816475B2

Reaction notes

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