Methanesulfonyl chloride → 3-(4-Bromophenyl)propyl methanesulphonate

HRID 217775

Reaction equation

HRID 217775 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([O:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 196884663-(4-Bromophenyl)propyl methanesulphonateYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(4-Bromophenyl)propan-1-ol (500 g, 2.30 mol) and diisopropylethylamine (312 g, 2.40 mol) in anhydrous dichloromethane (4 L) at 0˜5° C. was added dropwise methanesulphonyl chloride (280 g, 2.40 mol) slowly. After addition, the reaction mixture was stirred for 1 hour at 0˜5° C. The reaction mixture was washed with brine (1 L) twice. The organic phase was concentrated in vacuo to afford the subtitle compound (i) (667 g). HPLC Retention Time=1.353 min.

Workup

  1. additionAfter addition
  2. washThe reaction mixture was washed with brine (1 L) twice
  3. concentrationThe organic phase was concentrated in vacuo

Sources & evidence

ORD record
ord-1f92c5e26ddd484ea11e7af9ea1e0168
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Linked notes

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