Ammonium Chloride → HCID 59428415, compound

HRID 503906Notes

Reaction equation

HRID 503906 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([CH3:10])[CH:3]=1.[S:11](Cl)([CH3:14])(=[O:13])=[O:12].[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][S:11]([CH3:14])(=[O:13])=[O:12])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 59428415HCID 59428415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of (4-bromo-2-methyl-phenyl)-methanol (46.65 g, 0.2320 mol) in DCM (500 mL) at −15° C. was added mesyl chloride (20.65 mL, 0.2668 mol) followed by TEA (37.04 mL, 0.2668 mol). The reaction was stirred at −15° C. for 1.5 hour. A saturated solution of NH4Cl was then added at −15° C. and the resulting mixture was extracted with DCM. The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to afford methanesulfonic acid 4-bromo-2-methyl-benzyl ester as a white solid in quantitative yield (65 g), which was used directly in step 3 without further purification.

Workup

  1. extractionthe resulting mixture was extracted with DCM
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9f16ba67637240f6aa2526fac196a139
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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