1-Bromo-2-[(2,2-dimethoxyethyl)sulfanyl]benzene → 7-Bromobenzo[b]thiophene

HRID 1372147Notes

Reaction equation

HRID 1372147 reaction equation
CO[CH:3](OC)[CH2:4][S:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Br:12]>ClC1C=CC=CC=1>[Br:12][C:7]1[C:6]2[S:5][CH:4]=[CH:3][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 210717771-Bromo-2-[(2,2-dimethoxyethyl)sulfanyl]benzene

Product 1

HCID 120455387-Bromobenzo[b]thiopheneYield 89%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a 500 ml 3-neck flask was weighed out 15 g of polyphosphoric acid (PPA) followed by chlorobenzene (250 ml). After the mixture was heated to reflux (2-bromo-phenylsulfanyl)-acetaldehyde dimethylacetal (8.0 g in 60 ml chlorobenzene, 28.9 mmol) was added dropwise over 2.5 h via addition funnel and refluxed for an additional 24 h. After the reaction cooled it was filtered through a silica plug and concentrated to 6.04 g amber colored oil. Further purification by column chromatography (100% hexanes) afforded 5.47 g (89%) product as a clear oil: 1H NMR (300 MHz, DMSO-d6): δ 7.37 (1H, t, J=7.8 Hz), 7.63 (2H, m), 7.90 (1H, d, J=5.5 Hz), 7.94 (1H, d, J=7.9 Hz).

Workup

  1. customTo a 500 ml 3-neck flask was weighed out
  2. temperatureAfter the mixture was heated
  3. additionwas added dropwise over 2.5 h via addition funnel
  4. temperaturerefluxed for an additional 24 h
  5. temperatureAfter the reaction cooled it
  6. filtrationwas filtered through a silica plug
  7. concentrationconcentrated to 6.04 g amber colored oil
  8. customFurther purification by column chromatography (100% hexanes)

Sources & evidence

ORD record
ord-f340254426844f2a823f14c97b273db5
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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