Boron tribromide → HCID 12133345, compound

HRID 2414918Notes

Reaction equation

HRID 2414918 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, CH(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-12a5db61d4da447c9f57f127026f500b
Source dataset
uspto-grants-2004_11
Patent number
US06815555B2

Reaction notes

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