Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Formate | HCID 2723810 | — |
| Reactant | Methyl 2-acetoxy-4-(bromomethyl)benzoate | HCID 21840999 | — |
| Solvent | Dichloromethane ethylacetate | HCID 21226138 | — |
| Solvent | HCID 86745966 | HCID 86745966 | — |
| Product | HCID 54078316 | HCID 54078316 | 49.5% |
Reaction Steps
A solution containing 2-acetoxy-4-(bromomethyl) benzoic acid methyl ester (1.34g, 4.67 mmol, RN 13339-10-1) and sodium formate (0.795 g, 11.7 mmol) In EtOH:DMSO:H2O (2:2:1, 93 mL) was heated at 100° C. for 16 h. The reaction was cooled to ambient temperature, diluted with 10% CH2Cl2 /EtOAc (100 mL), washed with brine (3×), dried (Na2SO4) and concentrated. The crude product was purified on Biotage KP-Sil eluting with 20% acetone/hexane to give 0.518 g (49%) of the title compound as a clear oil. 1H NMR (DMSO-d6) δ 2.28 (s, 3H), 3.80 (s, 3H), 4.57 (d, 2H), 5.45 (br, t, 1H), 7.16 (s, 1H), 7.33 (d, 1H), 7.91 (d, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06063815 |
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| Source dataset | uspto-grants-2000_05 |
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| ORD ID | ord-dd20d84b21d24c4fb154a5a3a72c1a6b |
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| Source note | uspto-grants-2000_05 |
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