Water → (3-Fluorophenyl)(4-hydroxyphenyl)methanone

HRID 494821Notes

Reaction equation

HRID 494821 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water3×HCID 25134Boron tribromideHCID 13467539(3-Fluorophenyl)(4-methoxyphenyl)methanone

Product 1

HCID 11356363(3-Fluorophenyl)(4-hydroxyphenyl)methanoneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

(3-fluorophenyl)(4-methoxyphenyl)methanone (1.0 g, 4.34 mmol) in 50 mL DCM at −78° C. while stirring was treated with 1M boron tribromide (13.03 mL, 13.03 mmol) dropwise over 20 minutes. The mixture was allowed to warm to 25° C. and stir for 18 hours. The mixture was treated with water (1 mL) and stirred for 5 minutes, followed by additional water (2 mL) and stirred for 10 minutes, and finally treated with more water (50 mL) and stirred for 20 minutes. The mixture was then extracted with DCM (50 mL×2). The organic layers were combined, dried, filtered, and the filtrate evaporated under reduced pressure. The residue was purified by flash chromatography to provide the title compound (0.69 g, 74% yield). 1HNMR (300 MHz, CD3OD) δ 6.92 (d, 2H, J=8.9 Hz), 7.26 (m, 1H), 7.41-7.58 (m, 3H), 7.79 (d, 2H, J=8.9 Hz); MS (DCI) m/z 217 (M+H)+, 234 (M+NH4)+.

Workup

  1. stirringstirred for 5 minutes
  2. stirringstirred for 10 minutes
  3. stirringstirred for 20 minutes
  4. extractionThe mixture was then extracted with DCM (50 mL×2)
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate evaporated under reduced pressure
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-52581e40a4374c608363938395ec384d
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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