Hexane → [4-(Benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol

HRID 1009872Notes

Reaction equation

HRID 1009872 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[CH2:25]([O:32][C:33]1[C:40]([Br:41])=[CH:39][C:36]([CH:37]=[O:38])=[C:35]([CH3:42])[CH:34]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:25]([O:32][C:33]1[C:40]([Br:41])=[CH:39][C:36]([CH:37]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=2)[OH:38])=[C:35]([CH3:42])[CH:34]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 155094031-Bromo-4-[2-(methoxymethoxy)ethyl]benzeneHCID 866384374-(Benzyloxy)-5-bromo-2-methylbenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 67304665[4-(Benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a tetrahydrofuran solution (1 L) of 1-bromo-4-[2-(methoxymethoxy)ethyl]benzene (50.2 g, 0.205 mol) was added dropwise under nitrogen atmosphere at −78° C. a 2.6 M n-butyllithium solution in hexane (78.8 mL, 0.205 mol), and the mixture was stirred for 15 minutes at the same temperature. Then a tetrahydrofuran solution (150 mL) of 4-benzyloxy-5-bromo-2-methyl benzaldehyde (56.9 g, 0.195 mol) was added dropwise over an hour, and the mixture was stirred for 30 minutes at the same temperature. To the reaction solution was added a saturated aqueous solution of ammonium chloride, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride and brine, and dried with anhydrous magnesium sulfate. The drying agent was filtered off, and the solvent was evaporated under reduced pressure to obtain [4-(benzyloxy)-5-bromo-2-methylphenyl][4-[2-(methoxymethoxy)ethyl]phenyl]methanol.

Workup

  1. stirringthe mixture was stirred for 30 minutes at the same temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7b0c26a023574ec3a3131ea2641a66bf
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

Loading…