Sodium Formate → HCID 54078316, compound

HRID 1107929Notes

Reaction equation

HRID 1107929 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[O:12][C:13](=[O:15])[CH3:14].C([O-])=[O:18].[Na+]>CCO.CS(C)=O.O.C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:18])=[CH:6][C:5]=1[O:12][C:13](=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 2723810Sodium FormateHCID 21840999Methyl 2-acetoxy-4-(bromomethyl)benzoate

Product 1

HCID 54078316HCID 54078316, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 21226138Dichloromethane ethylacetateSolventHCID 86745966HCID 86745966, compoundSolvent

Conditions

Temperature
100 °C

Procedure

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).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. washwashed with brine (3×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was purified on Biotage
  6. washKP-Sil eluting with 20% acetone/hexane

Sources & evidence

ORD record
ord-dd20d84b21d24c4fb154a5a3a72c1a6b
Source dataset
uspto-grants-2000_05
Patent number
US06063815

Reaction notes

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