Chloromethyl Methyl Ether → HCID 68755004, compound

HRID 1753969Notes

Reaction equation

HRID 1753969 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[O:13][CH2:14]OC.Br[C:18]1C=CC(OC(F)(F)F)=C[C:19]=1O.[CH3:30][CH2:31][N:32](C(C)C)[CH:33](C)[CH3:34].C([Cl:42])OC>C(Cl)Cl.O>[Cl-:42].[F:12][C:9]([F:10])([F:11])[O:8][C:5]1[CH:6]=[CH:7][CH:2]=[C:3]2[C:4]=1[CH2:18][CH2:19][C:14]1([O:13]2)[CH2:34][CH2:33][NH2+:32][CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 177507422-Bromo-5-(trifluoromethoxy)phenolHCID 68755432HCID 68755432, compound

Product 1

HCID 68755004HCID 68755004, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Bromo-2-(methoxymethoxy)-4-(trifluoromethoxy)benzene To a cold solution of 2-bromo-5-(trifluoromethoxy)phenol (50 g, 195 mmol) and Hunig's base (120 mL, 687 mmol) in CH2Cl2 (100 mL) at −78° C. (frozen as a white cake) was added MOM-Cl (35 mL, 461 mmol). The white cake was warmed to room temperature and stirred overnight. The mixture was diluted with water (150 mL), the mixture was stirred for 15 min and extracted with CH2Cl2 (2×). The CH2Cl2 extracts were combined, washed with brine, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by column chromatography on SiO2 (isocratic 10% EtOAc/hexanes) to afford the title product as a colorless oil. 1H NMR (400 MHz, acetone-d6): δ 7.74 (d, 1 H), 7.22 (d, 1 H), 6.99 (dd, 1 H), 5.40 (s, 2 H), 3.52 (s, 3 H).

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with CH2Cl2 (2×)
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography on SiO2 (isocratic 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-416bc602c53547838097a76d05704bf2
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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