alpha-Bromo-o-chlorotoluene → HCID 58914708, compound

HRID 1297756Notes

Reaction equation

HRID 1297756 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[NH:6]2.C(N=P1(N(CC)CC)N(C)CCCN1C)(C)(C)C.[Cl:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:12])[C:5](=[O:11])[N:6]2[CH2:34][C:33]1[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=1[Cl:31]

Participants

6

Reactant 3

HCID 11905alpha-Bromo-o-chlorotolueneHCID 960474-ChloroisatinHCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine

Product 1

HCID 58914708HCID 58914708, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Partially dissolve 4-chloro isatin (118 mg, 0.65 mmol) in acetonitrile (4 mL). Add 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine (0.207 ml, 0.72 mmol) and after 5 min add 2-chlorobenzyl bromide (0.084 mL, 0.65 mmol). After 4 h dilute with ethyl acetate (50 mL) and wash with 1N HCl (2×20 mL), water, and brine. Dry (Na2SO4), filter and concentrate in vacuo to give 188 mg (94%) of the title compound as crude material as a red solid. MS (ES): m/z=306 (M+1).

Workup

  1. washwash with 1N HCl (2×20 mL), water, and brine
  2. dry with materialDry (Na2SO4)
  3. filtrationfilter
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-507fb7703df8486f936ad5d2b3b0842a
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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