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

HRID 1646348Notes

Reaction equation

HRID 1646348 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, 3 H, OCH3), 3.98 (s,3 H, OCH3), 4.28 (s,2 H, CH2 --Ar), 7.15 (d,1 H), 7.22 (s,1 H), 7.56 (m,2 H), 7.93 (d,1 H), 8.19 (dd, 1 H): 8.73 (d,1 H).

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-07ffe88c78794048b6a7e5c1b9c1fed2
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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