Hydrochloric Acid → 4-Bromo-4,4-difluorobutyl methanesulfonate

HRID 618188Notes

Reaction equation

HRID 618188 reaction equation
[Br:1][C:2]([F:8])([F:7])[CH2:3][CH2:4][CH2:5][OH:6].C(N(CC)CC)C.[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl>C(OCC)C>[CH3:16][S:17]([O:6][CH2:5][CH2:4][CH2:3][C:2]([Br:1])([F:8])[F:7])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27362724-Bromo-4,4-difluorobutan-1-ol

Product 1

HCID 218503894-Bromo-4,4-difluorobutyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of 4-bromo-4,4-difluorobutanol (0.57 g) in dry diethylether (5 cm3) was cooled to 0° C. Maintaining this temperature, triethylamine (1.7 cm3) was added. After ten minutes methanesulfonyl chloride (0.3 cm3) was added and the mixture stirred for a further hour at 0° C. The reaction mixture was poured into 2M hydrochloric acid (2 cm3) and diethylether (20 cm3). The organic phase was separated, washed with saturated brine, then passed through a plug of silica gel eluting with further diethylether. The diethylether fractions were evaporated under reduced pressure to give a light yellow oil (0.705 g). 1H NMR: δ 2.04-2.18(2H,m); 2.46-2.64(2H,m); 3.04(3H,s); 4.32(2H,t).

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with saturated brine
  4. customThe diethylether fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-da9bb7294eb847da815b36120d83890c
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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