Triethylamine → 4-bromo-5-[4-(chloromethyl)phenyl]-1-(2-methylpropyl)-1H-benzotriazole

HRID 2281058Notes

Reaction equation

HRID 2281058 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=1.CS([Cl:27])(=O)=O.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][Cl:27])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68657365{4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol

Product 1

HCID 867119834-bromo-5-[4-(chloromethyl)phenyl]-1-(2-methylpropyl)-1H-benzotriazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]phenyl}methanol (234 mg, 0.650 mmol) in dichloromethane (5 ml) at 0° C. was treated with methanesulfonyl chloride (0.056 ml, 0.715 mmol), followed by the dropwise addition of triethylamine (0.181 ml, 1.299 mmol). After 2 hours, the mixture was purified via silica gel chromatography (acetone/dichloromethane gradient), providing the titled compound as white solid. LRMS m/z (M+H) 377.9 and 379.9 found, 378.03 and 380.03 required.

Workup

  1. customthe mixture was purified via silica gel chromatography (acetone/dichloromethane gradient)

Sources & evidence

ORD record
ord-147307433e744ddea439e8e3eb83bb14
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

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