Potassium Carbonate → HCID 59760041, compound

HRID 1879131Notes

Reaction equation

HRID 1879131 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:18][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=2)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 15730468HCID 15730468, compound

Product 1

HCID 59760041HCID 59760041, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of ethyl 5-hydroxy-2-methylbenzoate (39.06 g, 217 mmol), 3-chlorobenzyl bromide (31.3 ml, 238 mmol) and potassium carbonate (44.9 g, 325 mmol) in N,N-dimethylformamide (1000 ml) was stirred at room temperature for 18 hours. The reaction was then filtered, diluted with ethyl acetate (2 L), washed with water (2 L then 3×1 L) and brine (1 L), filtered through a hydrophobic frit and concentrated to give the title compound as a dark yellow oil (68.61 g) which was used without further purification. MS (ES+) [C17H1735ClO3+H]+ 305. 1H-NMR (400 MHz, d6-DMSO) δ 1.31 (3H, t, J 7.2), 2.42 (3H, s), 4.28 (2H, q, J 7.2), 5.14 (2H, 2), 7.13-7.16 (1H, m), 7.19-7.23 (1H, m), 7.33-7.45 (4H, m), 7.54-7.55 (1H, m).

Workup

  1. filtrationThe reaction was then filtered
  2. additiondiluted with ethyl acetate (2 L)
  3. washwashed with water (2 L
  4. filtration3×1 L) and brine (1 L), filtered through a hydrophobic frit
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd54ee1c8b564b939e37502db6a542d4
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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