Triethylamine → HCID 69143570, compound

HRID 2055585Notes

Reaction equation

HRID 2055585 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][OH:5].[F:11][C:12]([F:18])([F:17])[S:13](Cl)(=O)=[O:14].C(N(CC)CC)C.COP(OC)OC>CCOCC>[F:11][C:12]([F:18])([F:17])[S:13]([O:5][CH2:4][C:3]1[C:6]([F:10])=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])=[O:14]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8472Trimethyl phosphiteHCID 79000Trifluoromethanesulfonyl chlorideHCID 918682-Chloro-6-fluorobenzyl alcohol

Product 1

HCID 69143570HCID 69143570, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-chloro-6-fluorobenzyl alcohol (0.50 g, 3.1 mmol) in ether (5 mL) at −10 C was added trifluoromethyl sulphonyl chloride, followed by a mixture of triethylamine (0.411 mL, 3.88 mmol) and trimethylphosphite (0.458 mLm, 3.88 mmol)) in ether (5 mL). The resulting mixture was stirred for 16 hours at room temperature and then partitioned between ether and water. The organic extract was washed with aq. HCl (0.5N), sat. aq. NaHCO3 and dried (MgSO4). The solvent was evaporated in vacuo to afford 2-chloro-6-fluorobenzyl trifluoromethanesulfinate as an oil. 1H NMR (400 MHz, CDCl3)2δ 7.38 (1H, dt, J=6 and 8 Hz) 7.28 (1H, d, J=8 Hz), 7.08 (1H, dt, J=1, 8 Hz), 5.53 (1H, dd, J=1.8 and 11.1 Hz), 5.30 (1H, dd, J=0.7 and 11.1 Hz) ppm.

Workup

  1. custompartitioned between ether and water
  2. extractionThe organic extract
  3. washwas washed with aq. HCl (0.5N), sat. aq. NaHCO3
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-17a55771519646378087a6879f1fbe58
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

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