Triethylamine → 3-(4-Bromophenyl)propyl methanesulphonate

HRID 2390550Notes

Reaction equation

HRID 2390550 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(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH3:19][S:20]([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:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 105606143-(4-Bromophenyl)propan-1-ol

Product 1

HCID 196884663-(4-Bromophenyl)propyl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(4-bromophenyl)propan-1-ol (6.17 g, 28.69 mmol) in dichloromethane (40 ml) was added triethylamine (4.80 ml, 34.42 mmol) and methanesulfonyl chloride (2.68 ml, 34.42 mmol). Reaction mixture stirred at RT under nitrogen overnight. The reaction mixture was evaporated to dryness and partitioned between EtOAc (50 mL) and water (25 mL), the aqueous portion was extracted with EtOAc (2×25 mL). Combined organics washed with 2M hydrochloric acid (2×25 mL) and saturated brine (25 mL). The organic was dried over magnesium sulfate, filtered and evaporated to afford the sub-title compound. Yield: 8.60 g

Workup

  1. customReaction mixture
  2. customThe reaction mixture was evaporated to dryness
  3. custompartitioned between EtOAc (50 mL) and water (25 mL)
  4. extractionthe aqueous portion was extracted with EtOAc (2×25 mL)
  5. washCombined organics washed with 2M hydrochloric acid (2×25 mL) and saturated brine (25 mL)
  6. dry with materialThe organic was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-7688ad37928e4666932128bd26f35406
Source dataset
uspto-grants-2012_09
Patent number
US08273774B2

Reaction notes

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