Water → HCID 10708738, compound

HRID 2111452Notes

Reaction equation

HRID 2111452 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Br[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=1.O>CN(C)C(=O)C>[I:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][S:3][C:1](=[O:4])[CH3:2])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9542584-Iodobenzyl bromideHCID 23670855Potassium ethanethioate

Product 1

HCID 10708738HCID 10708738, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a general procedure (Zheng et al. (1999) Tetrahedron Lett. 40: 603-606), potassium thioacetate (2.20 g, 19.3 mmol) was added to a solution of 4-(bromomethyl)-1-iodobenzene (4.80 g, 16.2 mmol) in anhydrous N,N-dimethylacetamide (15 mL). The mixture was stirred overnight at rt, poured into water, and extracted with CH2Cl2. The combined organic extracts were washed with water, dried (Na2SO4) and evaporated. The resulting brown oil was distilled (90° C., 0.005 mmHg) to obtain a pale-yellow solid which solidified after a few days (4.68 g, 99%). mp 40-41° C.; 1H NMR δ 2.37 (s, 3H), 4.07 (s, 2H), 7.07, 7.64 (AA′BB′, 2×2H); 13C NMR δ 31.09, 33.6, 93.5, 131.6, 138.2, 138.4, 195.5; FAB-MS obsd 291.9425, calcd exact mass 291.9419; Anal. Calcd. for C9H9IOS: C, 37.00; H, 3.11; I, 43.44; S, 10.98. Found: C, 37.39; H, 3.13; I, 43.04; S, 11.26.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. distillationThe resulting brown oil was distilled (90° C., 0.005 mmHg)
  6. customto obtain a pale-yellow solid which
  7. waitsolidified after a few days

Sources & evidence

ORD record
ord-52ea6342795c40db8213a47e9e780bec
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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