Carbon tetrabromide → 2,2-Dibromo-1-(4,4-dimethylthiochroman-6-yl)ethylene

HRID 840461Notes

Reaction equation

HRID 840461 reaction equation
[CH3:1][C:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=O)[CH:10]=2)[S:5][CH2:4][CH2:3]1.[C:15](Br)(Br)([Br:17])[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Zn].ClCCl>[Br:16][C:15]([Br:17])=[CH:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[S:5][CH2:4][CH2:3][C:2]2([CH3:14])[CH3:1]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 152843084,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde

Product 1

HCID 226194372,2-Dibromo-1-(4,4-dimethylthiochroman-6-yl)ethylene

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

5 g (24.2 mmol) of 4,4-dimethyl-6-thiochromancarboxaldehyde, prepared in Example 11(a), and 50 ml of dichloromethane were introduced into a round-bottomed flask. 16.1 g (48.4 mmol) of carbon tetrabromide, 12.7 g (48.4 mmol) of triphenylphosphine and 3.16 g (48.4 mmol) of zinc powder were successively added and stirring was carried out at room temperature for two hours. The reaction mixture was evaporated and the residue obtained purified by chromatography on a silica column eluted with hexane. 7.75 g (88%) of the expected compound were recovered.

Workup

  1. additionwere introduced into a round-bottomed flask
  2. customThe reaction mixture was evaporated
  3. customthe residue obtained
  4. custompurified by chromatography on a silica column
  5. washeluted with hexane
  6. custom7.75 g (88%) of the expected compound were recovered

Sources & evidence

ORD record
ord-17add07c339d4053863ef6d162eb2b32
Source dataset
uspto-grants-2002_04
Patent number
US06368608B1

Reaction notes

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