Dimethylformamide → HCID 59855504, compound

HRID 2375973Notes

Reaction equation

HRID 2375973 reaction equation
COC(=O)CC[C:6]1C=C[S:8][CH:7]=1.[Br:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.[C:21]([O-:24])([O-])=[O:22].[Cs+].[Cs+].[CH3:27]N(C=O)C>>[CH3:27][O:24][C:21](=[O:22])[CH2:6][CH2:7][S:8][CH2:17][C:16]1[CH:19]=[CH:20][C:13]([Br:12])=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 685274-Bromobenzyl bromideHCID 9793962methyl 3-thien-3-yipropionate

Product 1

HCID 59855504HCID 59855504, compoundYield 87%

Procedure

A solution of 3-thiolpropanoic acid methyl ester (1.2 g, 10 mmol) and 4-bromobenzyl-bromide (2.5 g, 10 mmol) in DMF (20 mL) was cooled to 0° C. and treated with Cs2CO3 (3.9 g, 12 mmol). After stirred for 2 h, the reaction was quenched with 5% HCl (25 mL) and diluted with ethyl acetate (50 mL). After seperation, the aqueous layer extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with sat. aq NaCl, dried over MgSO4 and concentrated. Purification by flash column chromatography (2-5% ethyl acetate in heptane) provided 3-(4-bromophenylmethylsulfanyl)-propanoic acid methyl ester (2.5 g, 87%) as white solid. 1H NMR (CDCl3), 7.43 (d, J=8 Hz, 2 H), 7.20 (d, J=8 Hz, 2 H), 3.68 (s, 5 H), 2.67 (m, 2 H), 2.56 (t, J=6 Hz, 2 H).

Workup

  1. customthe reaction was quenched with 5% HCl (25 mL)
  2. additiondiluted with ethyl acetate (50 mL)
  3. customAfter seperation
  4. extractionthe aqueous layer extracted with ethyl acetate (3×15 mL)
  5. washThe combined organic layers were washed with sat. aq NaCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (2-5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5d99a4976d834c7ca9110fd3bdc99718
Source dataset
uspto-grants-2008_12
Patent number
US07465825B2

Reaction notes

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