Sodium Carbonate → 3-Bromo-2-methoxyphenol

HRID 435508Notes

Reaction equation

HRID 435508 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](C=O)[C:3]=1[O:10][CH3:11].[Na].FC(F)(F)C(OO)=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.C(OCC)C>[Br:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([OH:16])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 5360545SodiumHCID 10290812Trifluoroperacetic acidHCID 110638083-BROMO-2-METHOXYBENZALDEHYDE

Product 1

HCID 218775343-Bromo-2-methoxyphenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.037 g 2-bromo-6-formyl-anisole in 1 ml methylene chloride is treated with 0.54 sodium dibasic phosphate and 1.3 ml trifluoroperacetic acid, stirred overnight, treated with 10% aqueous sodium carbonate (5 ml) and 5 ml diethyl ether, stirred for 1.5 hours, and partitioned between water and ether. The ether portion is extracted with 1 N aqueous sodium hydroxide, the hydroxide extracts acidified and then extracted with ether. Concentration of the ether extracts affords 3-bromo-2-methoxyphenol.

Workup

  1. stirringstirred for 1.5 hours
  2. custompartitioned between water and ether
  3. extractionThe ether portion is extracted with 1 N aqueous sodium hydroxide
  4. extractionextracted with ether

Sources & evidence

ORD record
ord-b0f8a5db8c604ab4b783bc5c034821f7
Source dataset
uspto-grants-1983_08
Patent number
US04401824

Reaction notes

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