1,3-Propanediol → HCID 68808464, compound

HRID 2249377Notes

Reaction equation

HRID 2249377 reaction equation
[F:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[B:11]([OH:13])[OH:12].[CH2:14](O)[CH2:15][CH2:16]O>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[B:11]1[O:13][CH2:16][CH2:15][CH2:14][O:12]1

Participants

4

Reactant 2

HCID 104421,3-PropanediolHCID 46739436(4-Fluoro-2H-1,3-benzodioxol-5-yl)boronic acid

Product 1

HCID 68808464HCID 68808464, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoro-3,4-methylenedioxyphenylboronic acid (1.4 g, 7.6 mmol) was slurried in toluene and propane-1,3-diol (0.6 g, 7.9 mmol) and the mixture heated under reflux for 0.5 hour. The mixture was cooled, filtered through glass wool and concentrated to give 2-(2-fluoro-3,4-methylenedioxyphenyl)-[1,3,2]-dioxaborinane (1.6 g, 7.1 mmol): 1H NMR (DMSO-d6): δ 7.12 (dd, 1H, J=7.8, 5.7 Hz), 6.75 (d, 1H), 6.09 (s, 2H), 4.06 (t, 4H), 1.98 (m, 2H).

Workup

  1. temperatureunder reflux for 0.5 hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through glass wool
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0e12b69efba4caca183c540a4057db3
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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