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

HRID 714592Notes

Reaction equation

HRID 714592 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=1[C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[CH:18]=1>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[C:15](=[O:25])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=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

Boron tribromide (1M in DCM, 48.0 mL, 48.0 mmol) was added dropwise 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. 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 by silica gel chromatography 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 by silica gel chromatography

Sources & evidence

ORD record
ord-4ec1f0e4d7b04af681d387ceb627f197
Source dataset
uspto-grants-2015_11
Patent number
US09187460B2

Reaction notes

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