Methyl 4-(bromomethyl)benzoate → HCID 21476912, compound

HRID 2293585Notes

Reaction equation

HRID 2293585 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1.Br[CH2:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1>>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH2:27][C:28]3[CH:29]=[CH:30][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:36][CH:37]=3)[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)(=[O:16])=[O:15])=[O:12])=[CH:4][C:3]=2[O:2]1

Participants

3

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 21476920HCID 21476920, compound

Product 1

HCID 21476912HCID 21476912, compoundYield 84%

Procedure

Using the general procedure described in Example 6 the dianion derived from the product of Example 1 (2.503 g; 6.93 mmol) was alkylated with methyl 4-bromomethylbenzoate. The crude reaction mixture was partitioned between EtOAc and 10% aqueous NaHSO4, separated dried and evaporated. The residue was purified on a silica gel flash chromatography eluted with CHCl3 -MeOH--NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 2.987 g (84%) of the title compound.

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between EtOAc and 10% aqueous NaHSO4
  3. customseparated
  4. customdried
  5. customevaporated
  6. customThe residue was purified on a silica gel flash chromatography
  7. washeluted with CHCl3 -MeOH
  8. customEvaporation of the purified fractions
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-a0f4940561674d06956a183dbde437e3
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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