Water → 4-Methoxybenzo[d][1,3]dioxole

HRID 1179224Notes

Reaction equation

HRID 1179224 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[C:4]=1[OH:10].Br[CH2:12]Cl.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]2[O:10][CH2:12][O:9][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6333BromochloromethaneHCID 136223-Methoxycatechol

Product 1

HCID 5924784-Methoxybenzo[d][1,3]dioxole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-benzene-1,2-diol (1.161 g, 8.28 mmol) in DMF (10 mL) was added to bromo-chloro-methane (611 ul, 1.1 equivalents) and stirred at 90 degrees Celsius for 4 hours. The mixture was poured into water and extracted with dichloromethane. The organic layer was poured thru a phase separator cartridge and concentrated to dryness. The crude product is a yellow liquid. The liquid was purified by column chromatography yielding 1.21 g, (96%). 1H-NMR (DMSO, 500 MHz) 6.7 (t, 1H), 6.63 (d, 1H), 6.58 (d, 1H), 5.97 (s, 2H), 3.83 (s, 3H)HPLC (method A) 2.86 min.

Workup

  1. extractionextracted with dichloromethane
  2. additionThe organic layer was poured thru a phase separator cartridge
  3. concentrationconcentrated to dryness
  4. customThe liquid was purified by column chromatography
  5. customyielding 1.21 g, (96%)
  6. customs, 3H)HPLC (method A) 2.86 min.

Sources & evidence

ORD record
ord-b76f1394950c4580a504f32f244b457c
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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