Triethylamine → Tert-butyl 3-bromo-5-{[(methylsulfonyl)oxy]methyl}benzoate

HRID 2173181Notes

Reaction equation

HRID 2173181 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH2:15][OH:16])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH2:15][O:16][S:18]([CH3:17])(=[O:20])=[O:19])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58096191Tert-butyl 3-bromo-5-(hydroxymethyl)benzoate

Product 1

HCID 86693004Tert-butyl 3-bromo-5-{[(methylsulfonyl)oxy]methyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a DCM (20 mL) solution of tert-butyl 3-bromo-5-(hydroxymethyl)benzoate (1.2 g, 4.2 mmol) was added methanesulfonyl chloride (0.62 g, 5.5 mmol) and triethylamine (1.2 mL, 8.4 mmol) at 0° C. The mixture was allowed to stir for 16 hours. TLC showed clean conversion. The reaction was diluted with DCM (100 mL), washed with 0.1 N HCl (100 mL) and brine, dried over sodium sulfate, and concentrated to afford tert-butyl 3-bromo-5-{[(methylsulfonyl)oxy]methyl}benzoate as a light yellow oil, which was used without further purification.

Workup

  1. washwashed with 0.1 N HCl (100 mL) and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-88a5b421f62d42f59566b270abf9c679
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…