Boron tribromide → HCID 57656322, compound

HRID 911264Notes

Reaction equation

HRID 911264 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][CH:8]=1)=[O:4].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]([F:15])([F:16])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 885647HCID 885647, compound

Product 1

HCID 57656322HCID 57656322, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve under nitrogen atmosphere 2,2,2-trifluoro-N-(4-methoxybenzyl)-acetamide (11.6 g, 50 mmol) in DCM (250 mL). Cool to 0° C. in an ice bath. Add dropwise 1M boron tribromide in DCM (100 mL, 100 mmol) and stir for 20 min after addition. Warm to ambient temperature and stir for 16 h. Cool the reaction mixture in an ice bath and quench very carefully with saturated aqueous NaHCO3. Separate the organic layer. Extract the aqueous layer twice with chloroform. Dry the combined organic extracts over-Na2SO4 and concentrate in vacuo to obtain the desired intermediate (8.8 g, 40 mmol). MS (ES−) m/z: 218 (M−H)−.

Workup

  1. additionafter addition
  2. temperatureWarm to ambient temperature
  3. stirringstir for 16 h
  4. temperatureCool the reaction mixture in an ice bath
  5. customquench very carefully with saturated aqueous NaHCO3
  6. customSeparate the organic layer
  7. extractionExtract the aqueous layer twice with chloroform
  8. dry with materialDry the combined organic extracts over-Na2SO4
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-e3c564851de041cdb026329729fe75cc
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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