Water → 4-Bromo-1-(chloromethyl)-2-methylbenzene

HRID 1625932Notes

Reaction equation

HRID 1625932 reaction equation
CS([Cl:5])(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]O)=[C:9]([CH3:15])[CH:8]=1.C(N(CC)CC)C.O>ClCCl>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][Cl:5])=[C:9]([CH3:15])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 200723584-Bromo-1-(chloromethyl)-2-methylbenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (171 mL, 2.11 mol) is added over 30 minutes to a mixture of (4-bromo-2-methyl-phenyl)methanol (250 g, 1.24 mol) and triethylamine (304 mL; 2.11 mol) in dichloromethane (2500 mL) cooled in ice/water. The mixture is allowed to warm to ambient temperature and is stirred for 16 hours. Water (5000 mL) is added and the product is extracted with dichloromethane (2×7000 mL). The combined organic layers are washed with saturated aqueous NaCl solution (5000 mL) and dried over Na2SO4. Filtration and concentration under reduced pressure provides a residue which is passed through a silica pad (eluting with hexane and ethyl acetate) to provide the title compound (234 g; 86% yield).

Workup

  1. extractionthe product is extracted with dichloromethane (2×7000 mL)
  2. washThe combined organic layers are washed with saturated aqueous NaCl solution (5000 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and concentration under reduced pressure
  5. customprovides a residue which
  6. washis passed through a silica pad (eluting with hexane and ethyl acetate)

Sources & evidence

ORD record
ord-b23f5a8e88da4c89b0e5599992a5d400
Source dataset
uspto-grants-2014_07
Patent number
US08785404B2

Reaction notes

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