Boron tribromide → HCID 22402551, compound

HRID 18453Notes

Reaction equation

HRID 18453 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].CCO.O.B(Br)(Br)Br>Cl>[CH2:12]([C:10]1[CH:11]=[C:3]([OH:2])[C:4](=[CH:8][CH:9]=1)[C:5]([OH:7])=[O:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 19096565Water ethanolHCID 68586125HCID 68586125, compound

Product 1

HCID 22402551HCID 22402551, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 2-methoxy-4-nonyl benzoic acid (600 mg; 2.15 mmol) was refluxed overnight in 6 M HCl [50% (w/w) EtOH/H2O; 35 mL). The reaction mixture was extracted with EtOAc (3×) dried (MgSO4), filtered and evaporated to dryness. The crude ester was dissolved in CH2Cl2 (10 mL), cooled to −10° C. and then added 1 M BBr3 (CH2Cl2; 10 mL; 10 mmol). The reaction mixture was allowed to warm to room temperature overnight and then poured onto H2O. Succeeding extraction with EtOAc, drying (MgSO4), filtering, evaporation to dryness and column chromatography (SiO2) yielded 130 mg (23%) product. Mp. 94-97° C.

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (3×)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. dissolutionThe crude ester was dissolved in CH2Cl2 (10 mL)
  6. temperatureto warm to room temperature overnight
  7. additionpoured onto H2O
  8. extractionextraction with EtOAc
  9. dry with materialdrying (MgSO4)
  10. filtrationfiltering
  11. customevaporation to dryness and column chromatography (SiO2)

Sources & evidence

ORD record
ord-df1219b1706e4fbcb7cf89bb9c4bdd97
Source dataset
uspto-grants-2010_06
Patent number
US07741352B2

Reaction notes

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