Hydrochloric Acid → 1204344-35-3

HRID 420331Notes

Reaction equation

HRID 420331 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH:10]([CH3:12])[CH3:11])[CH:3]=1.[Li]CCCC.CCCCCC.CN([CH:27]=[O:28])C.Cl>C1COCC1>[CH:10]([C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[CH:27]=[O:28])([CH3:12])[CH3:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8058HexaneHCID 54315784HCID 54315784, compoundHCID 178418339Butyllithium

Product 1

HCID 468336541204344-35-3

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-bromo-3-isopropyl-5-methoxy-benzene (1.06 g, 4.63 mmol) in dry THF (10 mL) was cooled to −78° C. under nitrogen atmosphere. A 1.6 M solution of nBuLi in hexane (2.9 mL, 4.63 mmol) was added at once, followed within 1 min by DMF (0.356 mL, 4.63 mmol). After 1 min the mixture was poured onto 10 mL 1N aq. HCl, stirred for 5 min and extracted with TBME. The organic phase was washed with brine, dried with MgSO4 and evaporated to give the title compound sufficiently pure for further use: TLC (AcOEt-hexane 1:9) Rf=0.40; HPLC RtH1=2.97 min; ESIMS [M+H]+=179; 1H NMR (400 MHz, CDCl3): δ 9.95 (s, 1H), 7.36 (s, 1H), 7.22 (s, 1H), 7.05 (s, 1H), 3.85 (s, 3H), 2.96 (heptet, 1H), 1.29 (d, 6H).

Workup

  1. extractionextracted with TBME
  2. washThe organic phase was washed with brine
  3. dry with materialdried with MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-5f6d103eb30d424d9623132c2a476a74
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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