1-Bromo-2-methylpropane → HCID 22149719, compound

HRID 1824482Notes

Reaction equation

HRID 1824482 reaction equation
[Mg].[CH2:2](Br)[CH:3]([CH3:5])[CH3:4].[F:7][C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[O:11]>CCOCC>[CH3:4][CH:3]([CH3:5])[CH2:2][CH:10]([OH:11])[C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[F:7]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropane3×HCID 67970o-Fluorobenzaldehyde2×HCID 5462224Magnesium

Product 1

HCID 22149719HCID 22149719, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a 3 necked round bottom flask (100 ml), equipped with a dropping funnel reflux condenser and thermometer pocket, placed magnesium turnings (1.45 gm 0.0604 mole) and flame dried the apparatus. Dry diethyl ether (15 ml.) was added to Mg. Turning, Isobutyl bromide (6.57 ml, 8.28 gm, 0.0645 mole) was taken in 5 ml of dry ether and added drop wise to the Mg turnings. As soon as ether starts boiling (in a few minutes) the reaction was cooled using ice-salt and continued the addition of isobutyl bromide. After complete addition of isobutyl bromide continued for another 20 minutes. o-Fluro benzaldehyde (4.25 ml, 5.0 gm, 0.0403 mole) in 10 ml of ether was added drop wise at −10° C. (around ½ hr). After the completion of addition of fluoro benzaldehyde continued the stirring for 1 hr and the reaction was quenched with ice-cooled saturated ammonium chloride solution (30 ml), the solid separated is filtered off, the filtrate is extracted with ethyl acetate (20×1, 10×2 ml) dried over sodium sulphate and concentrated to yield 6.54 gm of crude product (GC showed area of 85% purity). The crude product on vacuum distillation gave 3.93 gm (54.2%) of pure 3-methyl-1-(2-fluoro phenyl)butylalcohol (12) and impure product ˜2.87 gm containing 3-methyl-1-(2-fluoro phenyl)butylalcohol (12) 60% and byproduct (o-fluoro benzylalcohol) 40%. 1HNMR CDCl3 (spectrum 11): 0.96(d, 6H), 1.55(m, 1H), 1.75(m, 2H), 1.95 (bs, 1H), 5.05(m, 1H), 7.0(m, 1H), 7.20(m, 2H), 7.45(m, 1H)

Workup

  1. customIn a 3 necked round bottom flask (100 ml), equipped with a dropping funnel
  2. temperaturereflux condenser
  3. temperatureflame
  4. customdried the apparatus
  5. additionDry diethyl ether (15 ml.) was added to Mg
  6. custom(in a few minutes)
  7. temperaturewas cooled
  8. customstirring for 1 hr
  9. customthe reaction was quenched with ice-
  10. temperaturecooled saturated ammonium chloride solution (30 ml)
  11. customthe solid separated
  12. filtrationis filtered off
  13. extractionthe filtrate is extracted with ethyl acetate (20×1, 10×2 ml)
  14. dry with materialdried over sodium sulphate
  15. concentrationconcentrated
  16. customto yield 6.54 gm of crude product (GC showed area of 85% purity)
  17. distillationThe crude product on vacuum distillation

Sources & evidence

ORD record
ord-4638d1665c3c4b9dbaa555fe6b159e8a
Source dataset
uspto-grants-2006_05
Patent number
US07041830B2

Reaction notes

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