Dimethylformamide → HCID 1392506, compound

HRID 1757073Notes

Reaction equation

HRID 1757073 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CN(C=O)C>O>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:14]=[C:15]([CH2:19][C:20]([OH:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 74653(3-Bromophenyl)acetic acidHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acid

Product 1

HCID 1392506HCID 1392506, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

3-Hydroxymethylbenzeneboronic acid (1.8 g, 11.8 mmol), 3-bromophenylacetic acid (2.55 g, 11.8 mmol), tribasic potassium phosphate, (7.54 g, 35.5 mmol), DMF (55 ml), and water (20 ml) were degassed under nitrogen in a 250 ml flask fitted with a reflux condenser. Bis[triphenylphosphine]palladium(II) chloride (0.17 g, 0.24 mmol) was added. The mixture was degassed under nitrogen, and heated at 90° C. overnight, then acidified with 2N HCl, mixed with brine (15 ml), and extracted with methylene chloride (3×15 ml). The organic materials were combined, dried (MgSO4), then concentrated under reduced pressure which gave 3.0 g of 3-(3-hydroxymethylphenyl)phenyl acetic acid.

Workup

  1. customfitted with a reflux condenser
  2. customThe mixture was degassed under nitrogen
  3. additionmixed with brine (15 ml)
  4. extractionextracted with methylene chloride (3×15 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure which

Sources & evidence

ORD record
ord-5ac47172363a452c8718a7fad7df25aa
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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