Boron tribromide → HCID 67087112, compound

HRID 390389Notes

Reaction equation

HRID 390389 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([C:15]#[C:16][CH3:17])[CH2:11][C:12]([OH:14])=[O:13].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([C:15]#[C:16][CH3:17])[CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67087068HCID 67087068, compound

Product 1

HCID 67087112HCID 67087112, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-Fluoro-4-methoxy-phenyl)hex-4-ynoic acid (0.250 g, 1.12 mmol) is dissolved in DCM (5 mL) and boron tribromide (0.5 mL, 3.7 mmol) is added at −10° C. The mixture is stirred at ambient temperature for 1 hour. The solution is concentrated under reduced pressure, diluted with water, and extracted with EtOAc, dried with a drying agent, and concentrated under reduced pressure to give the title compound as a pale brown liquid (0.180 g, 76%). ESI/MS m/z 212 (M−H)−.

Workup

  1. concentrationThe solution is concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. customdried with a drying agent
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cbf539936207468890c02abb6a070e73
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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