Trifluoroacetic acid → 7,8-Di-methoxy-1-bromomethyl-1,3,4,5-tetrahydro-2-benzothiepin

HRID 223231Notes

Reaction equation

HRID 223231 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][SH:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(O[CH:18](OCC)[CH2:19][Br:20])C.FC(F)(F)C(O)=O>[N+](C)([O-])=O>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[CH:18]([CH2:19][Br:20])[S:14][CH2:13][CH2:12][CH2:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 205230623-(3,4-Dimethoxyphenyl)propane-1-thiol

Product 1

HCID 205226737,8-Di-methoxy-1-bromomethyl-1,3,4,5-tetrahydro-2-benzothiepin

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

A mixture of 0.67 g of 3-(3,4-dimethoxyphenyl)-1-propanethiol, 1.0 g of bromoacetaldehyde diethylacetal, 0.16 ml of trifluoroacetic acid, and 25 ml. of nitromethane as solvent is stirred at room temperature for 1 hour, stored overnight in the freezer, and then heated at 70° for 2 hours after an additional 0.05 ml trifluoroacetic acid is added. After cooling, the reaction mixture is extracted with methylene chloride and aqueous sodium bicarbonate. The organic layer is taken to dryness, and the residue is chromatographed one time on silica gel with methylene chloride as eluent and a second time with 10% ethyl acetate/Skellysolve B as eluent to yield 7,8-di-methoxy-1-bromomethyl-1,3,4,5-tetrahydro-2-benzothiepin.

Workup

  1. additionis added
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with methylene chloride and aqueous sodium bicarbonate
  4. customthe residue is chromatographed one time on silica gel with methylene chloride as eluent

Sources & evidence

ORD record
ord-8750764482a046b8ae0d0e58ffcea0f1
Source dataset
uspto-grants-1982_10
Patent number
US04352805

Reaction notes

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