tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 21476905, compound

HRID 2293586Notes

Reaction equation

HRID 2293586 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:33]=[CH:32][C:31]([C:34]2[CH:46]=[CH:45][CH:44]=[CH:43][C:35]=2[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[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:33]=[CH:32][C:31]([C:34]4[CH:46]=[CH:45][CH:44]=[CH:43][C:35]=4[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:30][CH:29]=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 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 21476920HCID 21476920, compound

Product 1

HCID 21476905HCID 21476905, compoundYield 69%

Procedure

Using the general procedure described in Example 6 the dianion derived from the product of Example 1 (0.419 g; 1.16 mmol) was alkylated with tert-butyl 2-(4-bromomethylphenyl)benzoate. 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 0.501 g (69%) 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-129e8f4214fd4c1fa76cfdc46005f0ed
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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