Chloromethyl Methyl Ether → HCID 68759899, compound

HRID 1753970Notes

Reaction equation

HRID 1753970 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9]OC)[CH:3]=1.Br[C:13]1C=C(O)C=C[CH:18]=1.[CH3:20][CH2:21][N:22](C(C)C)[CH:23](C)[CH3:24].C([Cl:32])OC>C(Cl)Cl.O>[Cl-:32].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:13][CH2:18][C:9]1([O:8]2)[CH2:24][CH2:23][NH2+:22][CH2:21][CH2:20]1

Participants

7

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 115633-BromophenolHCID 81531DiisopropylethylamineHCID 103309501-Bromo-3-(methoxymethoxy)benzene

Product 1

HCID 68759899HCID 68759899, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-Bromo-3-(methoxymethoxy)benzene To a solution of 3-bromophenol (10 g, 57.8 mmol) and Hunig's base (35.7 mL, 205 mmol) in CH2Cl2 (30 mL) at −78° C., was added MOM-Cl (10.98 mL, 145 mmol). The mixture was warmed to room temperature and stirred overnight. The mixture was diluted with water (150 mL), stirred for 15 min and extracted with CH2Cl2 (2×). The CH2Cl2 extract was washed with brine, dried (Na2SO4), filtered and concentrated to give a yellow oil. The material was purified by column chromatography on SiO2 (gradient from 0 to 20% EtOAc/hexanes) to give the title compound as a colorless oil.

Workup

  1. stirringstirred for 15 min
  2. extractionextracted with CH2Cl2 (2×)
  3. extractionThe CH2Cl2 extract
  4. washwas washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil
  9. customThe material was purified by column chromatography on SiO2 (gradient from 0 to 20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-975b41f35e334278b4c3dc2f3f983a58
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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