Acetyl chloride → 3-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoro-methyl)phenoxy)propan-1-ol

HRID 517984Notes

Reaction equation

HRID 517984 reaction equation
C(Cl)(=O)C.[CH3:5][C:6]1([CH3:34])[C:10]([CH3:12])([CH3:11])[O:9][B:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][O:23]C3CCCCO3)=[C:15]([C:30]([F:33])([F:32])[F:31])[CH:14]=2)[O:7]1>CO>[CH3:11][C:10]1([CH3:12])[C:6]([CH3:5])([CH3:34])[O:7][B:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][OH:23])=[C:15]([C:30]([F:32])([F:33])[F:31])[CH:14]=2)[O:9]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 672941484,4,5,5-tetramethyl-2-(4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane

Product 1

HCID 672942723-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoro-methyl)phenoxy)propan-1-olYield 101.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Acetyl chloride (14.26 ml) was added to MeOH (150 ml) at 0° C. and stirred for 10 minutes. The above mixture was added to 4,4,5,5-tetramethyl-2-(4-(3-(tetrahydro-2H-pyran-2-yloxy)propoxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane (43 g) in MeOH (300 ml) and stirred at 50° C. for 1.5 hours. The solvent was removed under reduced pressure, DCM was added to the residue and it was basified with sodium bicarbonate, washed with water, and the DCM was removed under reduced pressure to give expected compound (35 g). 1H NMR (CDCl3) δ: 8.00 (s, 1H), 7.92 (d, 1H), 6.98 (d, 1H), 4.21 (t, 2H), 3.86 (t, 2H), 2.07 (quin, 2H), 1.34 (s, 12H).

Workup

  1. stirringstirred at 50° C. for 1.5 hours
  2. customThe solvent was removed under reduced pressure, DCM
  3. additionwas added to the residue and it
  4. washwashed with water
  5. customthe DCM was removed under reduced pressure

Sources & evidence

ORD record
ord-c4aea1c2fcc1428b86a8482c3c9b87ab
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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