Hydrochloric Acid → Ethanol, 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-, 1-methanesulfonate

HRID 30762Notes

Reaction equation

HRID 30762 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1([CH3:24])[C:11]([CH3:13])([CH3:12])[O:10][B:9]([C:14]2[CH:23]=[CH:22][C:17]([O:18][CH2:19][CH2:20][OH:21])=[CH:16][CH:15]=2)[O:8]1.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH3:1][S:2]([O:21][CH2:20][CH2:19][O:18][C:17]1[CH:22]=[CH:23][C:14]([B:9]2[O:8][C:7]([CH3:24])([CH3:6])[C:11]([CH3:12])([CH3:13])[O:10]2)=[CH:15][CH:16]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 231341922-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethan-1-ol

Product 1

HCID 86605506Ethanol, 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-, 1-methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.33 mL) was added to a mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethanol (0.92 g) and triethylamine (0.73 mL) in methylene chloride (18 mL), and the mixture was stirred at room temperature for 1 hr. 1 mol/L hydrochloric acid was added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (1.28 g).

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-10a5121a6df1477b98499ab765d550c4
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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