Boron tribromide → HCID 58674650, compound

HRID 1994160Notes

Reaction equation

HRID 1994160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:22])/[C:10](=[CH:13]/[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20]C)[CH:15]=2)/[CH2:11][CH3:12])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].B(Br)(Br)Br>C(Cl)Cl>[OH:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)/[CH:13]=[C:10](\[CH2:11][CH3:12])/[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:23]([F:26])([F:24])[F:25])[CH:4]=1)=[O:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58674703HCID 58674703, compound

Product 1

HCID 58674650HCID 58674650, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2E)-N-[4-chloro-3-(trifluoromethyl)phenyl]-2-(3-methoxybenzylidene)butanamide (216 mg, 0.54 mmol) in DCM (15 mL) was cooled to 0° C. under an atmosphere of argon. To this solution was added BBr3 (1M in DCM, 1.18 mL). The cooling bath was removed and the reaction mixture was allowed to warm to rt. After stirring for 2 h, the reaction was quenched by the addition of water. The mixture was extracted with EtOAc and the combined organic solutions were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was triturated with DCM and filtered to give the desired phenol (189 mg). 1H NMR (400 MHz, d4-MeOH): δ 8.19 (d, 1H), 7.91-7.87 (dd, 1H), 7.55 (d, 1H), 7.24-7.16 (m, 2H), 6.87-6.85 (m, 2H), 6.77-6.74 (dd, 1H), 2.63 (q, 2H), and 1.14 (t, 3H).

Workup

  1. customThe cooling bath was removed
  2. customthe reaction was quenched by the addition of water
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic solutions were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with DCM
  9. filtrationfiltered

Sources & evidence

ORD record
ord-852a63d9cb2b459a91f54fc224544f58
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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