Hydrochloric Acid → Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

HRID 425295

Reaction equation

HRID 425295 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1F.[Br:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[Br:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 79178Dimethyl 2-fluoroterephthalate

Product 1

HCID 57839250Dimethyl 2-(2-bromophenoxy)benzene-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-fluoro-terephthalic acid dimethyl ester 2j (10 g, 47.1 mmol), 2-bromophenol 1j (6.0 mL, 51.8 mmol) and potassium carbonate (7.16 g, 51.8 mmol) in N,N-dimethylformamide (100 mL) was heated at 100° C. for 36 h. The mixture was allowed to cool to rt, then poured into cold dilute hydrochloric acid (0.5 N, 350 mL). The product was extracted into EtOAc, washed with water (4×) and brine (1×) and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel using dichloromethane as the eluant. The crude product was isolated (10.5 g) and used without further purification in the subsequent reaction. MS: m/z 365 (MH+).

Workup

  1. temperatureto cool to rt
  2. extractionThe product was extracted into EtOAc
  3. washwashed with water (4×) and brine (1×)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9aa268fa9af64837b4fe9febf42eaf06
Source dataset
uspto-grants-2012_01
Patent number
US08106207B2

Linked notes

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