Bromine → HCID 21071786, compound

HRID 1372149Notes

Reaction equation

HRID 1372149 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[S:16][CH:15]=[CH:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Br:18]Br>C(Cl)Cl>[Br:18][C:12]1[C:13]2[CH:14]=[CH:15][S:16][C:17]=2[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 210717947-(4-Methoxyphenyl)benzo[b]thiophene

Product 1

HCID 21071786HCID 21071786, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −20° C. solution of 7-(4-methoxyphenyl)-1-benzothiophene (500 mg, 2.08 mmol) in CH2Cl2 (15 ml) was added Br2 (8.33 ml of 0.25 M stock in CH2Cl2, 2.08 mmol) over 45 minutes. The reaction was stirred for an additional 0.5 h, washed with water, dried over Na2SO4, passed through a silica plug and concentrated to give 660 mg (100%) of product as a yellow solid. Further purification was done by recrystalization from 3% EtOAc in hexanes: mp 103–104° C.; 1H NMR (300 MHz, DMSO-d6): δ 3.84 (3H, s), 7.12 (2H, d, J=8.7 Hz), 7.31 (1H, d, J=7.9 Hz), 7.54 (1H, d, J=5.6 Hz), 7.65 (2H, d, J=8.7 Hz), 7.72 (1H, d, J=7.9 Hz), 7.98 (1H, d, J=5.6 Hz).

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f2582f766fae44e8a40445cd55e617f5
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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