Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 1470059Notes

Reaction equation

HRID 1470059 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]CC)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 99964494-Bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene

Product 1

HCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenolYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Example 1B (747 g, 2.31 mol) in dichloromethane was added boron tribromide (1.15 kg, 4.62 mol) slowly at −78° C. The reaction mixture was allowed to rise to room temperature. When the reaction was complete as measure by TLC, the reaction was quenched with water. The mixture was extracted with dichloromethane. The organic layer was washed with aqueous solution of saturated sodium bicarbonate, water, brine, dried over Na2SO4, and concentrated. The residue was recrystallized in petroleum ether to give the title compound as a white solid (460 g, yield 68%). 1H NMR (CDCl3, 400 MHz): δ 7.23˜7.29 (m, 3H), 7.08 (d, J=8.8 Hz, 2H), 6.79 (d, J=8.8 Hz, 2H), 5.01 (s, 1H), 4.00 (s, 2H).

Workup

  1. customto rise to room temperature
  2. customthe reaction was quenched with water
  3. extractionThe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with aqueous solution of saturated sodium bicarbonate, water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was recrystallized in petroleum ether

Sources & evidence

ORD record
ord-7cd9c09a810847fe9f10983b28fbbea3
Source dataset
uspto-grants-2015_04
Patent number
US09006403B2

Reaction notes

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