Boron tribromide → 1-(2,5-Dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanone

HRID 2368887Notes

Reaction equation

HRID 2368887 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][C:4]=1[C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:11](=[O:21])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 43337366HCID 43337366, compound

Product 1

HCID 866828831-(2,5-Dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanoneYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2,5-dimethoxyphenyl)-2-(3-methoxyphenyl)ethanone (3.35 g, 11.7 mmol) in DCM (50 mL) at −78° C., BBr3 (1M in DCM, 48.0 mL, 48.0 mmol) was added dropwise. The reaction mixture was warmed to 0° C., stirred for 30 min, re-cooled to −78° C., and then quenched with methanol (15 mL). The reaction mixture was warmed to room temperature, concentrated under reduced pressure and purified on a silica gel column to give 1-(2,5-dihydroxyphenyl)-2-(3-hydroxyphenyl)ethanone (1.78 g, 62%) as a yellow solid. 1H NMR (DMSO-d6): δ 11.24 (s, 1H), 9.34 (s, 1H), 9.20 (s, 1H), 7.26 (m, 1H), 7.10 (t, 1H), 6.98 (dd, 1H), 6.83 (d, 1H), 6.70 (m, 3H), 4.24 (s, 2H).

Workup

  1. temperaturere-cooled to −78° C.
  2. customquenched with methanol (15 mL)
  3. temperatureThe reaction mixture was warmed to room temperature
  4. concentrationconcentrated under reduced pressure
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-21c4967498d943bd9ff1b9639753bc78
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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