Boron tribromide → HCID 21079760, compound

HRID 1375210Notes

Reaction equation

HRID 1375210 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][C:4]=1[O:15]C)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[C:4]([OH:15])[CH:5]=1)[CH3:14]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21079761HCID 21079761, compound

Product 1

HCID 21079760HCID 21079760, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-ethyl-3-methoxyphenylacetate (10; 3.0 g; 13.50 mmol) and CH2Cl2 (80 mL) was cooled to −78° C. and a solution of BBr3 (5.10 mL; 53.94 mmol; 1.0 M in CH2Cl2) over 30 min. After 1 h at −78° C. the reaction was allowed to warm to rt and stirred for 12 h. The reaction was cooled in an ice-water bath and the reaction quenched with 20 mL of water. The aqueous phase was extracted with CH2Cl2:EtOAc (4:1 v/v), dried (Na2SO4), filtered and evaporated. The crude product was purified by silica gel chromatography and eluted with a CH2Cl2:EtOAc gradient (100:1 to 100:4) to yield 12a (2.0 g; 71%): ms 209.2 (M+H)+.

Workup

  1. temperatureThe reaction was cooled in an ice-water bath
  2. customthe reaction quenched with 20 mL of water
  3. extractionThe aqueous phase was extracted with CH2Cl2:EtOAc (4:1 v/v)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluted with a CH2Cl2

Sources & evidence

ORD record
ord-537b378e97434d1bb1097b0ba54f3a9d
Source dataset
uspto-grants-2007_01
Patent number
US07166738B2

Reaction notes

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