Boron tribromide → HCID 66992863, compound

HRID 556367Notes

Reaction equation

HRID 556367 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 21827188HCID 21827188, compound

Product 1

HCID 66992863HCID 66992863, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 4.72 g (20 mMol) 6-methoxy-benzo[b]thiophene-3-carboxylic acid ethyl ester in 200 ml CH2Cl2 at −10° C., 40 ml of a 1 M solution of BBr3 in CH2Cl2 are added via syringe during 12 min. The solution is stirred for 3.5 h at −10 to 0° C., then diluted with 600 ml EtOAc and poured into 450 ml of a mixture of sat. NaHCO3 and ice. After 5 min, the aq. layer is separated off and extracted 3× with 120 ml EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and after addition of SiO2 concentrated. The resulting powder is put on top of a SiO2-column and the title compound eluted with hexan/EtOAc 4:1: m.p.: 128-129° C.; TLC(hexane/EtOAc 4:1): Rf=0.18.

Workup

  1. waitAfter 5 min
  2. customthe aq. layer is separated off
  3. extractionextracted 3× with 120 ml EtOAc
  4. washThe organic phases are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. additionafter addition of SiO2
  7. concentrationconcentrated
  8. washthe title compound eluted with hexan/EtOAc 4:1

Sources & evidence

ORD record
ord-99ecd3eb401b41ccb40ba935e05a36a0
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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