Water → 2-[2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl methanesulfonate

HRID 2243536Notes

Reaction equation

HRID 2243536 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[CH:16]=[C:15]([B:17]2[O:21][C:20]([CH3:23])([CH3:22])[C:19]([CH3:25])([CH3:24])[O:18]2)[CH:14]=[C:13]([CH3:26])[C:8]=1[O:9][CH2:10][CH2:11][OH:12].C(N(CC)CC)C.O>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2]([O:12][CH2:11][CH2:10][O:9][C:8]1[C:13]([CH3:26])=[CH:14][C:15]([B:17]2[O:21][C:20]([CH3:22])([CH3:23])[C:19]([CH3:25])([CH3:24])[O:18]2)=[CH:16][C:7]=1[CH3:6])(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 231340982-[2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethanol

Product 1

HCID 230907982-[2,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.14 mL) was added to a mixture of 2-[2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)phenoxy]ethanol (0.5 g) and triethylamine (0.29 mL) in methylene chloride (10 mL), and the mixture was stirred for 1 hr at room temperature. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over an hydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford the title compound (0.632 g).

Workup

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

Sources & evidence

ORD record
ord-c65f4255ce1849c7a5696966958e57f9
Source dataset
uspto-grants-2010_03
Patent number
US07674938B2

Reaction notes

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