Boron tribromide → HCID 66642760, compound

HRID 2108591Notes

Reaction equation

HRID 2108591 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([O:9]C)=[C:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([CH:11]([CH3:13])[CH3:12])[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66642876HCID 66642876, compound

Product 1

HCID 66642760HCID 66642760, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-6-fluoro-2-iso-propylanisole (0.92 g, 3.70 mmol) in CH2Cl2 (10.0 mL) at −78° C. was added BBr3 (5.5 mL, 5.5 mmol, 1.0 M in CH2Cl2). After 5 min, the reaction mixture was stirred at room temperature for 16 h, poured into ice (50 g) and extracted with ethyl acetate (20.0 mL). The organic layer was separated, dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford 4-bromo-6-fluoro-2-iso-propylphenol (0.90 g, 100%) as a dark oil, which was used for the next step without further purification: 1H NMR (300 MHz, CD3OD): δ 7.26 (d, J=10.5 Hz, 1H), 6.92 (d, J=10.5 Hz, 1H), 3.30 (m, 1H), 1.23 (d, J=6.6 Hz, 6H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.40.

Workup

  1. extractionextracted with ethyl acetate (20.0 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bf99eaa0a7244679b7a1860f9bad99bd
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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