Triethylamine → 3-Bromo-4-fluorobenzyl methanesulfonate

HRID 83876

Reaction equation

HRID 83876 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[F:8].CCN(CC)CC.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[CH3:18][S:19]([O:10][CH2:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Br:1])[CH:3]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27733513-Bromo-4-fluorobenzyl Alcohol

Product 1

HCID 598548133-Bromo-4-fluorobenzyl methanesulfonateYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-bromo-4-fluorophenyl)methanol (53 g, 0.258 mol) in DCM (500 mL) at 0° C. was added Et3N (108 mL, 775 mmol, 3 eq) and methanesulfonyl chloride (24 mL, 310 mmol, 1.2 eq) successively. After stirring 30 min, the reaction mixture was partitioned in DCM and water. The organic layer was dried over MgSO4 and evaporated in vacuo to give 3-bromo-4-fluorobenzyl methanesulfonate (60 g), which used to the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.65-7.62 (m, 1H), 7.37-7.33 (m, 1H), 7.16 (t, J=4.4 Hz, 1H), 5.17 (s, 2H), 2.99 (s, 3H).

Workup

  1. customthe reaction mixture was partitioned in DCM
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec7499c6f61a4e40a8ae183568bf4d73
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Linked notes

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