3-(Bromomethyl)thiophene → HCID 57064325, compound

HRID 981778Notes

Reaction equation

HRID 981778 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH:6]([CH3:8])[O-].[Na+].Br[CH2:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1.C[O:18]CCOC(O)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:8][O:18][CH2:11][C:12]1[CH:16]=[CH:15][S:14][CH:13]=1

Participants

5

Reactant 3

HCID 5207033-(Bromomethyl)thiopheneHCID 14367673HCID 14367673, compoundHCID 88434596HCID 88434596, compound

Product 1

HCID 57064325HCID 57064325, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of sodium methoxyethoxyethoxide (29.6 g, 0.2 mol) in methoxyethoxyethanol (100 ml) was added to a solution of 3-(bromomethyl)thiophene (12.4 g, 0.07 mol) in carbon tetrachloride (25 ml) and the mixture heated under reflux for 12 hours. Work-up as described in Example 1 gave a crude oil which was distilled under reduced pressure to yield 3-(methoxyethoxyethoxymethyl)thiophene (7.0 g, 46%), B.p. 136°-138° C./10 mm. Hg. (Found: C, 56.0; H, 7.0; S, 15.1. Calculated for C10H16O3S: C, 55.5; H, 7.4; S, 14.8%); EI m/e Intensity (%): 216 (12 M+), 97 (100, C4H3S.CH2); δH(CDCl3): 6.96-7.17 (3H, m), 4.45 (2H, s), 3.50 (4H, m), 3.40 (4H, m) and 3.26 (3H, s); δ C(CDCl3): 58.3, 66.1, 69.2, 70.2, 70.4, 71.7, 121.7, 125.2, 126.7, 139.6 ppm.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 12 hours
  3. customgave a crude oil which
  4. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-b0f6c3e5a64f40ff9d43b1d1a67eda06
Source dataset
uspto-grants-1991_02
Patent number
US04992559

Reaction notes

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