Hydrochloric Acid → Diisopropyl Ether

HRID 2263556Notes

Reaction equation

HRID 2263556 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[CH:8]=1.C(N([CH2:22][CH3:23])CC)C.Cl>ClCCl>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([Br:6])=[CH:8][C:9]=1[O:16][S:2]([CH3:1])(=[O:4])=[O:3])(=[O:15])[CH3:14].[CH:22]([O:15][CH:13]([CH3:10])[CH3:14])([CH3:23])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 107274031-(4-Bromo-2-hydroxyphenyl)ethan-1-one

Product 2

HCID 7914Diisopropyl EtherHCID 86071609Methanesulfonic acid 2-acetyl-5-bromophenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.42 ml of methanesulphonyl chloride are added dropwise to a solution of 10.0 g 1-(4-bromo-2-hydroxy-phenyl)ethanone [30186-18-6] and 13.0 ml of triethylamine in 200 ml dichloromethane at 0° C. The reaction mixture is worked up after 1 hour by pouring into 250 ml cold 1N HCl and extracting with tert-butyl methyl ether (2×)—the combined organic layers are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as light yellow crystals from the residue by re-crystallization from diisopropyl ether. Rf=0.51 (1:1 EtOAc-heptane). Rt=3.94 (gradient I). m.p. 62.0-62.1° C.

Workup

  1. extractionextracting with tert-butyl methyl ether (2×)—the combined organic layers
  2. washare washed successively with water and brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-56149856062c48e1bb3e06601d07058f
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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