Benzyl Bromide → HCID 59559917, compound

HRID 1177108Notes

Reaction equation

HRID 1177108 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([OH:16])[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate

Product 1

HCID 59559917HCID 59559917, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) was dissolved in DMF (50 mL). K2CO3 (6.48 g, 46.9 mmol) and benzyl bromide (2.80 mL, 23.6 mmol) were added. The reaction mixture was stirred at room temperature overnight, quenched with H2O (150 mL), and extracted with EtOAc (2×150 mL). The organic layers were dried over MgSO4 and concentrated to give a white solid (7.18 g, 98% yield) which was used as it is for the next step. 1H NMR (400 MHz, CDCl3) δ 7.34-7.46 (m, 5 H) 7.21 (s, 1 H) 7.08 (s, 1 H) 5.13 (s, 2 H) 3.90 (s, 3 H) 3.02 (s, 2 H) 1.49 (s, 6 H); LCMS for C19H20O4 m/z 313.20 (M+H)+.

Workup

  1. customquenched with H2O (150 mL)
  2. extractionextracted with EtOAc (2×150 mL)
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8987801e10424c14974996eeab07eb82
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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