Chloromethyl Methyl Ether → 2-Bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene

HRID 1037113Notes

Reaction equation

HRID 1037113 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10]1.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]1([O:14][CH2:24][O:25][CH3:26])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 726983321-(2-Bromo-4-methylphenyl)cyclopentanol

Product 1

HCID 866854782-Bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1-(2-bromo-4-methylphenyl)cyclopentanol (4.2 g, 16.5 mmol) in DCM (40 mL) at rt were successively added DIPEA (11 mL, 66 mmol) and MOMCl (2.5 mL, 33 mmol) over a 10 min period. The solution was stirred for 11 h at rt, and afterwards a NH4Cl-saturated aqueous solution (40 mL) was added. The aqueous phase was segregated, and the organic one was washed with water (30 mL), brine (30 mL), dried with anhydrous Na2SO4, filtered, and concentrated to give pure 2-bromo-1-(1-(methoxymethoxy)cyclopentyl)-4-methylbenzene (4.0 g, yield 81%).

Workup

  1. customat rt
  2. customover a 10 min
  3. washthe organic one was washed with water (30 mL), brine (30 mL)
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-def6618313d447bba76394d66887e6f2
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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