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Acetic Acid → 2-[(Benzenesulfonyl)methyl]-4-bromo-1-nitrobenzene

HRID 1990967
Notes
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Reaction equation

HRID 1990967 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].CC([O-])(C)C.[K+].C(O)(=O)C>C1COCC1.O.C([O-])(O)=O.[Na+]>[C:16]1([S:13]([CH2:12][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[N+:8]([O-:10])=[O:9])(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 114661-Bromo-4-nitrobenzeneHCID 81625((Chloromethyl)sulphonyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 124463822-[(Benzenesulfonyl)methyl]-4-bromo-1-nitrobenzeneYield 72.4%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×
HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1-bromo-4-nitrobenzene (5.05 g, 25 mmol) and chloromethyl-phenylsulfone (4.76 g, 25 mmol) in dry THF (50 mL) at −65° C. under nitrogen is added 1.0M KOtBu in THF (55 mL, 55 mmol). The deep purple reaction is allowed to warm to 0° C. over 1.5 hours and then treated with glacial acetic acid (4 mL). The reaction is diluted with water (100 mL) and saturated aqueous NaHCO3 (100 mL), and then extracted with CH2Cl2 (2×200 mL). The extracts are dried (MgSO4) and concentrated in vacuo to a light orange solid. Trituration with ethyl acetate and hexanes affords the title compound as a pale yellow solid (6.45 g, 72%). Mp: 143-144° C. MS (ES−): 354 (M−H).

Workup

  1. customThe deep purple reaction
  2. extractionextracted with CH2Cl2 (2×200 mL)
  3. dry with materialThe extracts are dried (MgSO4)
  4. concentrationconcentrated in vacuo to a light orange solid

Sources & evidence

ORD record
ord-fe9dc4e2b00e41eb9a3dc80adb2b4749
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07645752B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes