Bromine → 4-Bromo-2-(trifluoromethoxy)phenol

HRID 1916554Notes

Reaction equation

HRID 1916554 reaction equation
[Br:1]Br.[F:3][C:4]([F:14])([F:13])[O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][C:10]1[CH:9]=[CH:8][C:7]([OH:12])=[C:6]([O:5][C:4]([F:13])([F:14])[F:3])[CH:11]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 27772992-(Trifluoromethoxy)phenol

Product 1

HCID 117801514-Bromo-2-(trifluoromethoxy)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1.55 mL (30.3 mmol) bromine in 50 mL DCM is added dropwise to a solution of 5.0 g (28.1 mmol) 2-trifluoromethoxy-phenol in 70 mL DCM at −78° C. The reaction solution is heated to RT and stirred for a further 48 h. Then 70 mL Na2SO3 solution are added and the mixture is stirred until the orange colour has disappeared. The solution is diluted with DCM, the organic phase is washed with NaCl solution, dried over MgSO4 and the solvent is eliminated i.vac. The purification is carried out by column chromatography on silica gel (gradient: PE to PE:EtOAc 4:1).

Workup

  1. stirringthe mixture is stirred until the orange colour
  2. washthe organic phase is washed with NaCl solution
  3. dry with materialdried over MgSO4
  4. customThe purification

Sources & evidence

ORD record
ord-13f5a3f0ed484ad0a0485125f0c8bcd0
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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