1-(Bromomethyl)-3-chlorobenzene → HCID 58392702, compound

HRID 446850Notes

Reaction equation

HRID 446850 reaction equation
Cl.[F:2][C@@:3]12[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]3)[C@@H:10]([F:19])[CH2:9][C@H:8]1[C@@H:7]1[CH2:20][C@@H:21]3[C@:25]([C:26](=[O:30])[CH2:27][S:28][CH3:29])([C@@:6]1([CH3:31])[CH2:5][C@@H:4]2[OH:32])[CH2:24][NH:23][CH2:22]3.[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]Br>C(Cl)Cl>[Cl:33][C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37][N:23]1[CH2:24][C@:25]2([C:26](=[O:30])[CH2:27][S:28][CH3:29])[C@@H:21]([CH2:20][C@H:7]3[C@H:8]4[C@@:3]([F:2])([C@:16]5([CH3:17])[C:11]([C@@H:10]([F:19])[CH2:9]4)=[CH:12][C:13](=[O:18])[CH:14]=[CH:15]5)[C@@H:4]([OH:32])[CH2:5][C@@:6]32[CH3:31])[CH2:22]1

Participants

4

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 67352780HCID 67352780, compound

Product 1

HCID 58392702HCID 58392702, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 186 (103 mg, 0.211 mmol), 3-chorobenzylbromide (66.0 μl, 0.317 mmol) and TEA (88 μl, 0.633 mmol) in DCM (10 ml) is stirred under nitrogen at RT for 16 hours. The solution is diluted with DCM and washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated and the crude is purified by silica gel chromatography (eluent: DCM/MeOH 99/1). Trituration with petroleum ether affords the title compound (36 mg, 29.6% yield).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe solvent is evaporated
  5. customthe crude is purified by silica gel chromatography (eluent: DCM/MeOH 99/1)

Sources & evidence

ORD record
ord-9e8f1bdfe13a48cf99e8b921885ded75
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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