Chloromethyl Methyl Ether → HCID 86685468, compound

HRID 1037100Notes

Reaction equation

HRID 1037100 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:14])([CH2:12][CH3:13])[CH2:10][CH3:11].CCN(C(C)C)C(C)C.[CH2:24](Cl)[O:25][CH3:26].[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:14][CH2:24][O:25][CH3:26])([CH2:12][CH3:13])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 72698334HCID 72698334, compound

Product 1

HCID 86685468HCID 86685468, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 3-(2-bromo-4-methylphenyl)pentan-3-ol (6.0 g, 23.3 mmol) in DCM (20 mL) at rt were successively added DIPEA (8.1 mL, 47.4 mmol) and MOMCl (2.7 mL, 35.5 mmol) over a 10 min period. The solution was stirred 11 h at rt followed by addition of aqueous NH4Cl solution (100 mL). The aqueous phase was segregated, and the organic one was washed with water (100 mL), brine, dried with anhydrous Na2SO4, filtered, and concentrated to give pure 2-bromo-1-(3-(methoxymethoxy)pentan-3-yl)-4-methylbenzene (4.0 g, yield 57%).

Workup

  1. customat rt
  2. customover a 10 min
  3. washthe organic one was washed with water (100 mL), brine
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d943978f8128453c87a1448ae315cd5c
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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