1,4-Dibromobenzene → HCID 18669677, compound

HRID 1058998Notes

Reaction equation

HRID 1058998 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH:14]1([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])C=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.[O:30]1CCC[CH2:31]1>>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:31]([OH:30])[C:25]2[CH:22]=[CH:21][C:20]([O:19][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18]3)=[C:27]([O:28][CH3:29])[CH:26]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 78041,4-DibromobenzeneHCID 8028Tetrahydrofuran2×HCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 18669677HCID 18669677, compound

Procedure

To a solution of 1,4-dibromobenzene (25.72 g, 109 mmol) in dry tetrahydrofuran (50 ml) at isopropanolg/dry ice bath temperature under argon was added n-butyl lithium (43.6 ml of 2.5 M solution in hexane, 109 mmol) dropwise. This was stirred for one hour during which time a slurry formed. This slurry was added via cannula to a solution of 3-cyclopentoxy-4-methoxybenzaldehyde (20.0 g, 90.8 mmol) in dry THF (140 ml) at isopropanol/dry ice bath temperature. After one hour, the reaction was allowed to gradually warm to room temperature and stirred for an additional 4 h. The reaction was quenched with water then extracted three times with diethyl ether. The combined organic extract was washed successively with 1% hydrochloric acid, water, brine, then dried and evaporated. Purification by flash chromatography (silica gel, 17% ethyl acetate/83% hexane) provided the title compound as a pale white solid (36.78 g, 100% crude yield). MS (m/e): 359 [(M+1H2O)+]

Workup

  1. customformed
  2. waitAfter one hour
  3. stirringstirred for an additional 4 h
  4. customThe reaction was quenched with water
  5. extractionthen extracted three times with diethyl ether
  6. extractionThe combined organic extract
  7. washwas washed successively with 1% hydrochloric acid, water, brine
  8. customdried
  9. customevaporated
  10. customPurification by flash chromatography (silica gel, 17% ethyl acetate/83% hexane)

Sources & evidence

ORD record
ord-a3102574791045189e7958eb1bac3f87
Source dataset
uspto-grants-2003_02
Patent number
US06518306B1

Reaction notes

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