Water → 443982-73-8

HRID 252318Notes

Reaction equation

HRID 252318 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=C(OC)[C:10]=1[CH2:11][CH2:12]C)[CH2:6]O.P(Br)(Br)[Br:17].O.C[CH2:22][O:23][CH2:24][CH3:25]>>[CH3:22][O:23][C:24]1[CH:25]=[C:11]([CH:10]=[C:3]([O:2][CH3:1])[C:4]=1[CH:5]([CH3:8])[CH3:6])[CH2:12][Br:17]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 24614Phosphorus tribromideHCID 66842651HCID 66842651, compound

Product 1

HCID 66842814443982-73-8Yield 91.4%

Procedure

To 3,5-Dimethoxy-4-1-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-5b5d2247dec149aa820df96244066217
Source dataset
uspto-grants-2011_01
Patent number
US07868047B2

Reaction notes

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