Hydrochloric Acid → HCID 68702180, compound

HRID 2220456Notes

Reaction equation

HRID 2220456 reaction equation
[Br-].[Li+].C[C:4]1[CH:9]=[CH:8][C:7]([Mg]Br)=[CH:6][CH:5]=1.CCOCC.[CH2:17]([C:21]1[S:25][C:24]([C:26](=[O:30])[C:27](Cl)=[O:28])=[CH:23][CH:22]=1)[CH2:18][CH2:19][CH3:20].Cl>[Cu](Br)Br.C1COCC1>[CH2:17]([C:21]1[S:25][C:24]([C:26](=[O:30])[C:27]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:28])=[CH:23][CH:22]=1)[CH2:18][CH2:19][CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 82050Lithium BromideHCID 86609891HCID 86609891, compoundHCID 178418370HCID 178418370, compound

Product 1

HCID 68702180HCID 68702180, compound

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Into a flask containing THF (60 mL) was added copper (II) bromide (5.7 g, 40 mmol) followed by lithium bromide (6.8 g, 80 mmol). The reaction was cooled to 0° C. and a solution of 4-methyl-phenylmagnesium bromide (1N) in ether (48 mmol) was added dropwise. The reaction was stirred 10 min and a solution containing (5-butyl-thiophen-2-yl)-oxo-acetyl chloride was added dropwise over 20 min at 0° C. The reaction was poured into HCl 1N (aqueous) and extracted with ether. The organic layer was separated and washed with NaOH 2.5N (aqueous), then brine and dried over MgSO4, filtered and stripped. MS m/e 273 (M)−; 1HNMR (DMSO-d6, 300 MHz) δ 0.9 (t, 3H), 1.3 (m, 2H), 1.6 (m, 2H), 2.8 (t, 2H), 7.0 (s, 1H), 7.6 (t, 2H), 7.7 (s, 1H), 7.8 (m, 1H), 7.9 (d, 2H).

Workup

  1. additionwas added dropwise over 20 min at 0° C
  2. extractionextracted with ether
  3. customThe organic layer was separated
  4. washwashed with NaOH 2.5N (aqueous)
  5. dry with materialbrine and dried over MgSO4
  6. filtrationfiltered

Sources & evidence

ORD record
ord-59660e42763648e08ee254408e7d4719
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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