Water → Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

HRID 1756380Notes

Reaction equation

HRID 1756380 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[O:25][CH3:26].O>ClCCl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[CH2:14][C:10]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 124140845-Nitro-1-benzothiophene

Product 1

HCID 14763112Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stannic chloride (0.41 g.) was added to a stirred solution of 5-nitrobenzo[b]thiophene (0.28 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (0.61 g.) in dichloromethane (5 ml.). The mixture was heated under reflux for 18 hours. The cooled mixture was poured into water (10 ml.) and extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4) and evaporated. The oil was purified by flash chromatography on silica gel (100 ml.) eluting with 1:9 v/v ethyl acetate:hexane. The solid obtained was crystallized from hexane to give methyl 3-methoxy-4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate (I) as a solid (0.16 g., 30%); NMR: (250 MHz, CDCl3): 3.92(s, 3H, OCH3), 3.98(s,3H, OCH3), 4.28(s,2H, CH2 --Ar), 7.15 (d,1H), 7.22(s,1H), 7.56(m,2H), 7.93(d,1H), 8.19(dd, 1H); 8.73(d,1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionextracted with dichloromethane (2×20 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customThe oil was purified by flash chromatography on silica gel (100 ml.)
  7. washeluting with 1:9 v/v ethyl acetate
  8. customThe solid obtained
  9. customwas crystallized from hexane

Sources & evidence

ORD record
ord-503d7549078c4978bb166d118667de84
Source dataset
uspto-grants-1995_08
Patent number
US05440035

Reaction notes

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