Boron tribromide → HCID 90417900, compound

HRID 2177160Notes

Reaction equation

HRID 2177160 reaction equation
C[O:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][C:4]=1[C:20]([F:23])([F:22])[F:21].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[C:4]([C:20]([F:21])([F:22])[F:23])=[CH:5][C:6]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:8]=1[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 90418486HCID 90418486, compound

Product 1

HCID 90417900HCID 90417900, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 50-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed ethyl 3-[4-methoxy-3,5-bis(trifluoromethyl)phenyl]propanoate (270 mg, 0.78 mmol, 1.00 equiv), dichloromethane (5.0 mL). That was followed by adding BBr3 (1N in dichloromethane) (1.57 mL) dropwise at −78 degree C. The resulting solution was warmed to room temperature and stirred for 2 h at 25° C. The reaction progress was monitored by LCMS. The reaction was then quenched by the addition of 5 mL of water, extracted with 3×10 mL of dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:4). This resulted in 0.15 g (58%) of ethyl 3-[4-hydroxy-3,5-bis(trifluoromethyl)phenyl]propanoate as yellow oil. Mass spectrum (ESI, m/z): Calcd. for C13H12F6O3, 329.1 (M−H). found 329.1.

Workup

  1. customInto a 50-mL round-bottom flask (1 atm) purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of 5 mL of water
  4. extractionextracted with 3×10 mL of dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThis resulted in 0.15 g (58%) of ethyl 3-[4-hydroxy-3,5-bis(trifluoromethyl)phenyl]propanoate as yellow oil

Sources & evidence

ORD record
ord-85780353eed642df843f881c49d47a6c
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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