Water → (3-Chloro-2-hydroxyphenyl)-(2-hydroxyphenyl)methane

HRID 1111280Notes

Reaction equation

HRID 1111280 reaction equation
[Cl:1][C:2]1[C:3]([OH:17])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15]C)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:3]([OH:17])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22151939(3-Chloro-2-hydroxyphenyl)(2-methoxyphenyl)methane

Product 1

HCID 22151945(3-Chloro-2-hydroxyphenyl)-(2-hydroxyphenyl)methane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(3-Chloro-2-hydroxyphenyl)(2-methoxyphenyl)methane (3.98 g, 16 mmol) was dissolved in 100 ml of methylene chloride and 24 ml of 1M boron tribromide in methylene chloride (24 mmol) was added under nitrogen with stirring at ambient temperature. The mixture was allowed to react for 4 hours and then 100 ml of water was added slowly at ambient temperature. The organic layer was recovered and extracted with 2 N sodium hydroxide. The alkaline extract was acidified with 6 N hydrochloric acid and extracted with ether. The ether extract was dried over magnesium sulfate and concentrated by evaporation under reduced pressure to obtain 2.7 g (72 percent of theory) of the title compound. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. customto react for 4 hours
  2. customThe organic layer was recovered
  3. extractionextracted with 2 N sodium hydroxide
  4. extractionThe alkaline extract
  5. extractionextracted with ether
  6. extractionThe ether extract
  7. dry with materialwas dried over magnesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2ce2a07a312b4d0b94a9f89f4f29b886
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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