Water → HCID 58875081, compound

HRID 130372Notes

Reaction equation

HRID 130372 reaction equation
[CH3:1][C:2]([S:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:7])[C:3](=[O:6])[CH2:4][CH3:5].[Br-:13].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.O>C(Cl)Cl>[Br:13][CH:4]([CH3:5])[C:3](=[O:6])[C:2]([S:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:1])[CH3:7]

Participants

5

Reactant 3

HCID 962WaterHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58875078HCID 58875078, compound

Product 1

HCID 58875081HCID 58875081, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(1,1-dimethyl-2-oxobutyl)thio]acetic acid (0.3 g, 1.58 mmol) in CH2Cl2 (10 ml) was added phenyltrimethylammonium tribromide (0.62 g, 1.65 mmol) at 0° C. After stirring for 15 min, the solution was allowed to come to room temperature and stirring was continued for 1 h. Water (30 ml) was added and the aqueous layer was extracted with diethyl ether (15 ml). The combined organic layers were washed with brine (25 ml), dried over Na2SO4, filtered and concentrated in vacuo. The remaining oil was purified by flash chromatography (ethyl acetate-petroleum ether 1:1 containing 0.1% glacial acetic acid). Yield: 0.39 mg (91%). 1H-NMR (400 MHz, CDCl3): δ=1.15, 1.64 (2×s, 6H, C(CH3)2), 1.81 (d, 3H, J=7.0 Hz), 3.14, 3.21 (2×d, 2H, J=6.8 Hz), 5.07 (q, 1H, J=7.0 Hz) ppm. C8H13BrO3S (269.16, 267.98), HRMS: calcd (M+Na)+ 290.9661, found 290.9669.

Workup

  1. customto come to room temperature
  2. stirringstirring
  3. waitwas continued for 1 h
  4. extractionthe aqueous layer was extracted with diethyl ether (15 ml)
  5. washThe combined organic layers were washed with brine (25 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe remaining oil was purified by flash chromatography (ethyl acetate-petroleum ether 1:1 containing 0.1% glacial acetic acid)

Sources & evidence

ORD record
ord-745d28c25313418b8fec5c6040451005
Source dataset
uspto-grants-2008_06
Patent number
US07381743B2

Reaction notes

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