Methanol → Methyl 3-(bromoacetyl)benzoate

HRID 1815214Notes

Reaction equation

HRID 1815214 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2N=C(C3N=C(C4CCCCC4)NC=3COC34CC5CC(CC(C5)C3)C4)SC=2)[CH:5]=1.Br[C:40]([Br:42])=O.C[OH:44]>>[CH3:1][O:2][C:3](=[O:38])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=[O:44])[CH2:40][Br:42])[CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 79057Carbonyl bromideHCID 69745032HCID 69745032, compound

Product 1

HCID 13612769Methyl 3-(bromoacetyl)benzoate

Procedure

3-{2-[5-(Adamantan-1-yloxymethyl)-2-cyclohexyl-1H-imidazol-4-yl]-thiazol-4-yl}-benzoic acid methyl ester. 3-(2-Bromo-acetyl)-benzoic acid methyl ester was prepared as described by Schmied (Schmied, Gading, Monatshefte Chem. 1953, 84, 491). A solution of this bromoketone (0.44 g, 1.7 mmol) and the thioamide from step c (0.52 g, 1.4 mmol) in methanol (10 ml) was heated under reflux for 5 h. The solvent was evaporated and the residue taken up in ethyl acetate and washed with saturated aqueous sodium hydrogen carbonate (2×20 ml), brine (20 ml) then dried (MgSO4). The crude product was purified by flash chromatography (Silica, DCM/ethyl acetate 95:5-90:10). Yield 0.36 g (48%). 1H NMR (300 MHz, CDCl3) 9.25 (1H, br s), 8.64 (1H, s), 8.16 (1H, d), 8.01 (1H, d), 7.51 (2H, m), 5.17 (2H, s), 3.95 (3H, s), 2.79 (1H, m), 2.20 (3H, br s), 2.07 (2H, m), 1.90-1.36 (20H, m).

Workup

  1. temperatureunder reflux for 5 h
  2. customThe solvent was evaporated
  3. washwashed with saturated aqueous sodium hydrogen carbonate (2×20 ml), brine (20 ml)
  4. dry with materialthen dried (MgSO4)
  5. customThe crude product was purified by flash chromatography (Silica, DCM/ethyl acetate 95:5-90:10)

Sources & evidence

ORD record
ord-c6faf2097c2d4d2aa8fc5741909ba802
Source dataset
uspto-grants-2005_04
Patent number
US06878734B2

Reaction notes

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