Boron tribromide → HCID 12133345, compound

HRID 1765338Notes

Reaction equation

HRID 1765338 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:7]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:9]=1[O:10]C)([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:7]=[C:8]([CH:12]([CH3:14])[CH3:13])[C:9]=1[OH:10])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22644100HCID 22644100, compound

Product 1

HCID 12133345HCID 12133345, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3,5-diisopropyl-4-methoxyphenylacetate (100 mg) in dichloromethane (12 mL) at −78° C. was added a solution of boron tribromide (0.57 mL) in dichloromethane. The reaction mixture was stirred at −78° C. for 1 hour and at 0° C. for 1 hour, quenched by water, and extracted with dichloromethane. The combined organics were washed (brine), dried (MgSO4), filtered, and concentrated. Purification by preparative thin layer chromatography, with ethyl acetate:hexane:acetic acid (90:9:1) gave the title compound (24 mg); 1H-NMR (CDCl3) δ=1.25 (d, 12H, CH(CH3)2), 3.15 (m, 2H, CCH(CH3)2), 3.55 (S, 2H, CH2), 3.70 (S, 3H, OCH3), 6.98 (S, 2H, ArH)

Workup

  1. customquenched by water
  2. extractionextracted with dichloromethane
  3. washThe combined organics were washed (brine)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative thin layer chromatography

Sources & evidence

ORD record
ord-32142c7850bd403a8fd6219aa34378df
Source dataset
uspto-grants-2007_06
Patent number
US07226946B2

Reaction notes

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