Boron tribromide → HCID 66642760, compound

HRID 1170952Notes

Reaction equation

HRID 1170952 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 flier purification: 1H NMR (300 MHz, CD3OD): δ 7.26 (d, J=10.5 Hz, 1 H), 6.92 (d, J=10.5 Hz, 1 H), 3.30 (m, 1 H), 1.23 (d, J=6.6 Hz, 6 H); 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-425d7f9a4a6e412b9995cb50c0b00b92
Source dataset
uspto-grants-2010_11
Patent number
US07829552B2

Reaction notes

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