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

HRID 626231Notes

Reaction equation

HRID 626231 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. The extract was washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1 to 2/1) to give 536 mg (60%) 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. washThe extract was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=5/1 to 2/1)

Sources & evidence

ORD record
ord-546a96f3bdf040349c22dd3f69e806c2
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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