Chloromethyl Methyl Ether → 2-(6-Bromo-3-methoxy-2-methoxymethoxy-phenyl)-5,5-dimethyl-[1,3]dioxane

HRID 929111Notes

Reaction equation

HRID 929111 reaction equation
[Br:1][C:2]1[C:3]([CH:11]2[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[CH2:13][O:12]2)=[C:4]([OH:10])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.CCN(C(C)C)C(C)C.Cl[CH2:29][O:30][CH3:31]>C(Cl)Cl>[Br:1][C:2]1[C:3]([CH:11]2[O:12][CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][O:16]2)=[C:4]([O:10][CH2:29][O:30][CH3:31])[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 597618363-Bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol

Product 1

HCID 597618382-(6-Bromo-3-methoxy-2-methoxymethoxy-phenyl)-5,5-dimethyl-[1,3]dioxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 3-bromo-2-(5,5-dimethyl-[1,3]dioxan-2-yl)-6-methoxy-phenol in DCM (20 mL) was added DIEA (697 μL, 4 mmol), followed by addition of chloromethoxymethane (228 μL, 3 mmol). After it was stirred at the room temperature for 72 h, the reaction mixture was evaporated and the residue was partitioned between NaHCO3 (50 mL) solution and EtOAc (40 mL). The aqueous layer was extracted with EtOAc (3×10 mL) and the combined extracts were washed with brine and dried through Na2SO4. Evaporation of solvent afforded the title compound. 1H NMR (CDCl3) δ 0.80 (s, 3H), 1.45 (s, 3H), 3.57 (s, 3H), 3.65 (d, J=12 Hz, 2H), 3.79 (s, 3H), 3.80 (d, J=12 Hz, 2H), 5.11 (s, 2H), 6.00 (s, 1H), 6.76 (d, J=8 Hz, 1H), 7.32 (d, J=8 Hz, 1H).

Workup

  1. customthe reaction mixture was evaporated
  2. customthe residue was partitioned between NaHCO3 (50 mL) solution and EtOAc (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  4. washthe combined extracts were washed with brine
  5. dry with materialdried through Na2SO4
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-d164b3c94a3e4fcba144442f301fb8cf
Source dataset
uspto-grants-2016_03
Patent number
US09290503B2

Reaction notes

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