Methanol → 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

HRID 1522949Notes

Reaction equation

HRID 1522949 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C@H:8]([CH:11]([CH3:13])[CH3:12])[CH2:9]O)=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21].P(Br)(Br)([Br:24])=O.O.CO>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C@H:8]([CH:11]([CH3:13])[CH3:12])[CH2:9][Br:24])=[CH:5][C:4]=1[O:16][CH2:17][CH2:18][CH2:19][O:20][CH3:21]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24613Phosphorus oxybromideHCID 9835828(R)-2-[3-(3-Methoxypropoxy)-4-methoxybenzyl]-3-methylbutan-1-OL

Product 1

HCID 113258232-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzeneYield 79.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve (R)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl butanol (14.82 g, 50 mmol) in N,N-dimethyl formamide (234 ml), add phosphorus oxybromide (14.33 g, 50 mmol) in droplets slowly and control the temperature at 20° C. in that process, and then let them to react at 20° C. for 8 hours. Cool down to room temperature, and pour the reactant liquid into water (702 ml) slowly, extract with normal hexane for three cycles, combine the normal hexane layers, wash twice with saturated sodium bicarbonate and saturated sodium chloride respectively, dry the organic layer with anhydrous sodium sulfate, filter, and condense the filtrate so as to obtain 17 g of oily matter. Add 51 ml of methanol, control the product to crystallize at −10° C., filter, and then treat the filter cake by vacuum drying at room temperature, so as to obtain 14.3 g of white solid matter; the yield is 79.6%, mp: 51-53° C., chiral purity: ≧99.9%.

Workup

  1. customat 20° C.
  2. customto react at 20° C. for 8 hours
  3. extractionextract with normal hexane for three cycles
  4. washwash twice with saturated sodium bicarbonate and saturated sodium chloride respectively
  5. dry with materialdry the organic layer with anhydrous sodium sulfate
  6. filtrationfilter
  7. customcondense the filtrate so as
  8. customto obtain 17 g of oily matter
  9. customto crystallize at −10° C.
  10. filtrationfilter
  11. additiontreat the filter cake by vacuum
  12. customdrying at room temperature

Sources & evidence

ORD record
ord-42afa72089fa4faaa9482e9954a43ce8
Source dataset
uspto-grants-2015_07
Patent number
US09079839B2

Reaction notes

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