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

HRID 2243541Notes

Reaction equation

HRID 2243541 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-ce51b8c1a33e48a9a9d45933be1d3a38
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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