Water → 443982-73-8

HRID 2252344Notes

Reaction equation

HRID 2252344 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:14][CH3:15])[C:10]=1[CH:11]([CH3:13])[CH3:12])[CH2:6]O.P(Br)(Br)[Br:17].O>CCOCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:14][CH3:15])[C:10]=1[CH:11]([CH3:13])[CH3:12])[CH2:6][Br:17]

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 46928175(3,5-dimethoxy-4-propan-2-yl-phenyl)methanol

Product 1

HCID 66842814443982-73-8Yield 175.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 3,5-Dimethoxy-4-i-propylbenzyl alcohol (12.57 g, 59.8 mmol) in dry ether (100 mL) at 0° C. was added PBr3 (3.0 mL, 31.2 mmol) dropwise under nitrogen. The reaction was monitored by TLC. After the reaction was completed (˜4 h), water (180 mL) was added. The organic layer was separated and the aqueous layer was extracted with ether (3×50 mL). The extract was washed with water (20 mL), sat. Na2CO3 (20 mL), water (20 mL) and brine (20 mL), and dried over anhydrous sodium sulfate. Evaporation of the solution yielded pure bromide (14.93 g, 91.4%) as a white solid. 1HNMR (CDCl3, ppm): δ 1.29 (d, J=7.1 Hz, 6H), 3.64 (hept, J=7.1 Hz, 1H), 3.84 (s, 6H), 4.50 (s, 2H), 6.60 (s, 2H).

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ether (3×50 mL)
  4. washThe extract was washed with water (20 mL), sat. Na2CO3 (20 mL), water (20 mL) and brine (20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation of the solution

Sources & evidence

ORD record
ord-142c063c6097424fb06b9f88b3fa8fef
Source dataset
uspto-grants-2008_01
Patent number
US07321050B2

Reaction notes

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