Hydrochloric Acid → HCID 178490127, compound

HRID 720768Notes

Reaction equation

HRID 720768 reaction equation
[Mg].II.Br[C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([O:15][CH3:16])=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=1.[P:21]([O-:26])(OC)OC.Cl>C1COCC1.C1(C)C=CC=CC=1.O>[C:17]([C:7]1[CH:6]=[C:5]([PH:21](=[O:26])[C:5]2[CH:10]=[C:9]([C:11]([CH3:13])([CH3:14])[CH3:12])[C:8]([O:15][CH3:16])=[C:7]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=2)[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]=1[O:15][CH3:16])([CH3:20])([CH3:19])[CH3:18]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 5462224MagnesiumHCID 136915415-Bromo-1,3-di-tert-butyl-2-methoxybenzeneHCID 21884954Dimethylphosphite

Product 1

HCID 178490127HCID 178490127, compoundYield 27.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Under argon atmosphere, a solution of magnesium (4.0 g, 0.95 equivalents) and a small amount of iodine in THF (50 mL) was stirred at room temperature for 1 hour. After 4-bromo-2,6-di-tert-butylanisole (52 g, 0.175 mol) synthesized in Reference Example 2 was added at 46° C. to 53° C. thereto, the mixture was stirred at 5° C. for 1 hour. Then, dimethyl phosphite (11.4 g, 0.52 equivalents) was added and the mixture was stirred at 5° C. for 1 hour. After water (50 mL) was added at 3° C. and toluene (50 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An organic layer was washed successively with water (20 mL), a 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to obtain the title compound (11.6 g, pale yellowish white crystal). Yield 20.5%, mp. 166.1° C.

Workup

  1. additionwas added at 46° C. to 53° C.
  2. stirringthe mixture was stirred at 5° C. for 1 hour
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customto separate into layers
  5. washAn organic layer was washed successively with water (20 mL)
  6. dry with materiala 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate
  7. filtrationnaturally filtered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe residue was recrystallized from heptane

Sources & evidence

ORD record
ord-ac34e7535139423385828f0f73ee2ea8
Source dataset
uspto-grants-2006_11
Patent number
US07135582B2

Reaction notes

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