Boron tribromide → (4-(2-Bromoethoxy)-3-fluorophenyl)(4-hydroxyphenyl)methanone

HRID 626135Notes

Reaction equation

HRID 626135 reaction equation
B(Br)(Br)Br.[Br:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)=[O:16])=[CH:11][C:10]=1[F:25]>ClCCl>[Br:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[O:16])=[CH:11][C:10]=1[F:25]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 89656419(4-(2-Bromoethoxy)-3-fluorophenyl)(4-methoxyphenyl)methanone

Product 1

HCID 89656059(4-(2-Bromoethoxy)-3-fluorophenyl)(4-hydroxyphenyl)methanoneYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (0.5 mL, 5.29 mmol) was added to (4-(2-bromoethoxy)-3-fluorophenyl)(4-methoxyphenyl)methanone (930 mg, 2.63 mmol) in dichloromethane (6 mL) at 0° C. Stirring was continued at room temperature for 2 h under a nitrogen atmosphere. The reaction mixture was quenched with ice water and extracted with dichloromethane and the white suspension was filtered off. The organic layer was washed with water and brine and then dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by purification by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1 to 2/1) gave 536 mg (60% yield) of the subtitle compound as a beige solid. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J=8.4 Hz, 2H), 7.59 (d, J=12.4 Hz, 1H), 7.56 (d, J=8.0 Hz, 1H), 7.03 (dd, J=8.0 Hz, 8.0 Hz, 1H), 6.92 (d, J=8.4 Hz, 2H), 5.88 (s, 1H), 4.44 (t, J=6.4 Hz, 2H), 3.70 (t, J=6.4 Hz, 2H).

Workup

  1. customThe reaction mixture was quenched with ice water
  2. extractionextracted with dichloromethane
  3. filtrationthe white suspension was filtered off
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customSolvent evaporation under reduced pressure
  7. customfollowed by purification by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1 to 2/1)

Sources & evidence

ORD record
ord-82d7d5272485441aa423191617001fd0
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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