Benzyl Bromide → 4-{[4-(Benzyloxy)phenyl]sulfanyl}-2-chlorobenzaldehyde

HRID 272281Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:17]=[C:16](F)[CH:15]=[CH:14][C:11]=1[CH:12]=[O:13].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH2:25]([O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:16]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[C:10]([Cl:9])[CH:17]=2)=[CH:4][CH:3]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Conditions

Temperature: 50 °C

Procedure

p-hydroxythiophenol (2.12 g) was dissolved in N,N-dimethylformamide (40 mL). To this solution, 2-chloro-4-fluorobenzaldehyde (2.66 g) and potassium carbonate (4.64 g) were added and the mixture was stirred for 2 hours at 50° C. Subsequently, benzyl bromide (4.00 mL) was added and the mixture was stirred for 1.5 hours at 50° C. and then for 2.5 hours at 70° C. The reaction mixture was extracted with ethyl acetate and the extract was washed sequentially with water and a saturated aqueous solution of sodium chloride. The organic phase was then dried over anhydrous sodium sulfate. Following addition of water, the solvent was removed by distillation and the residue was purified on a silica gel column chromatography (hexane:ethyl acetate=10:1). This gave the desired product as a colorless solid (5.70 g).

Workup

stirringthe mixture was stirred for 1.5 hours at 50° C.
waitfor 2.5 hours at 70° C
extractionThe reaction mixture was extracted with ethyl acetate
washthe extract was washed sequentially with water
dry with materialThe organic phase was then dried over anhydrous sodium sulfate
additionaddition of water
customthe solvent was removed by distillation
customthe residue was purified on a silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record: ord-60d4b2ccd43c4cd2a2792257e2363693
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456157B2

Reaction notes

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