3-(Trifluoromethyl)phenol → 70743-66-7

HRID 1156844Notes

Reaction equation

HRID 1156844 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][CH:9]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>C(Cl)Cl>[F:13][C:10]([F:11])([F:12])[C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[O:3][CH2:18][CH2:17][CH2:16][CH2:15][Br:14]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 80561,4-DibromobutaneHCID 14798Sodium Hydroxide

Product 1

HCID 1283676370743-66-7Yield 80.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

267 ml of 1.6 N sodium hydroxide solution are added dropwise with stirring at 100° C. within 90 minutes to a mixture of 69.3 g of 3-hydroxybenzotrifluoride and 119 g of 1,4-dibromobutane. The mixture is stirred at this temperature for a further 5 hours and is then allowed to cool. 200 ml of methylene chloride are added, the organic phase is separated off, washed with dilute sodium hydroxide solution, dried over sodium sulfate and concentrated. The residue is distilled in vacuo. 102.6 g of 4-(3-trifluoromethylphenoxy)butyl bromide of b.p. 143° to 144° C. (13 mm Hg=1730 Pa) are obtained.

Workup

  1. temperatureto cool
  2. customthe organic phase is separated off
  3. washwashed with dilute sodium hydroxide solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. distillationThe residue is distilled in vacuo

Sources & evidence

ORD record
ord-dcd90ae8baa54f1e907abac5f4ae6a66
Source dataset
uspto-grants-1982_06
Patent number
US04337267

Reaction notes

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