Potassium Carbonate → HCID 69781516, compound

HRID 1761010Notes

Reaction equation

HRID 1761010 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O>[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][O:7][C:6](=[O:8])[C:5]1[C:4](=[CH:3][C:2]([O:1][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([F:14])[CH:16]=2)=[CH:10][CH:9]=1)[C:11]([O:13][CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([F:14])[CH:16]=1)=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 118814-Hydroxyphthalic acidHCID 680073-Fluorobenzyl bromide

Product 1

HCID 69781516HCID 69781516, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of 4-hydroxyphthalic acid (5.0 g, 27.5 mmol), 3-fluorobenzylbromide (31.14 g, 164.7 mmol) and potassium carbonate (15.18 g, 109.8 mmol) in THF:water (1:1, 200 mL) was heated under reflux for 72 h. After cooling to RT, the mixture was then half evaporated and the residue extracted with ethyl acetate (100 mL). The organic layer was then washed with brine, dried over sodium sulfate, filtered and evaporated. The mixture was then heated in a Kugelrohr apparatus (160° C. at 15 mmHg) to remove the excess 3-fluorobenzylbromide to leave the title compound (13.1 g, 94%) as a light yellow liquid. MS m/e=506.1 (M).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 72 h
  3. customhalf evaporated
  4. extractionthe residue extracted with ethyl acetate (100 mL)
  5. washThe organic layer was then washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. temperatureThe mixture was then heated in a Kugelrohr apparatus (160° C. at 15 mmHg)
  10. customto remove the excess 3-fluorobenzylbromide

Sources & evidence

ORD record
ord-bc0c032c62fa41bca32c2d02b03228a5
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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