Dimethylformamide → 8-Chloro-4,4-dimethylthiochroman-6-carbaldehyde

HRID 402809Notes

Reaction equation

HRID 402809 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[S:8][CH2:7][CH2:6][C:5]2([CH3:14])[CH3:13].[Li]CCCC.CN([CH:23]=[O:24])C>>[Cl:12][C:10]1[CH:11]=[C:2]([CH:23]=[O:24])[CH:3]=[C:4]2[C:9]=1[S:8][CH2:7][CH2:6][C:5]2([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 667649386-Bromo-8-chloro-4,4-dimethylthiochromanHCID 178418339Butyllithium

Product 1

HCID 866768178-Chloro-4,4-dimethylthiochroman-6-carbaldehyde

Procedure

Using essentially the same procedure as Example 5-20, Step 3, 6-bromo-8-chloro-4,4-dimethyl-3,4-dihydro-2H-thiochromene (954 mg, 3.27 mmol), n-BuLi (1.57 mL, 3.93 mmol) and DMF (1.01 mL, 13.1 mmol) afforded the desired product as a pale-yellow oil.

Sources & evidence

ORD record
ord-3489dc472502407298b694e9f83c8ba7
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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