tert-Butyl bromoacetate → HCID 15617528, compound

HRID 2352121Notes

Reaction equation

HRID 2352121 reaction equation
[Cl-].C([Al+]CC)C.[F:7][C:8]([F:32])([F:31])[C:9]1[CH:10]=[C:11]([S:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=2[CH:25]=[O:26])[CH:12]=[CH:13][CH:14]=1.Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>O1CCCC1.CCCCCC.[Zn].[Cu]Br>[OH:26][CH:25]([C:24]1[CH:27]=[CH:28][CH:29]=[CH:30][C:23]=1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][S:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:8]([F:31])([F:7])[F:32])[CH:10]=1)[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]

Participants

8

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 15617527HCID 15617527, compoundHCID 16686102Diethyl aluminum chloride

Product 1

HCID 15617528HCID 15617528, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 24593copper(I) bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of zinc dust (0.25 g, 3 mmoles) and copper (I) bromide (0.02 g, 0.129 mmoles) in distilled tetrahydrofuran (20 ml) was added a solution of diethylaluminum chloride (2.8 ml, 2.8 mmoles) in hexane while stirring under argon at 25° C. The resulting mixture was cooled to -20° C, and a solution of 2-[7-(3-trifluoromethylphenylthio)heptyl]benzaldehyde (1.08 g, 2.8 mmoles) and t-butyl bromoacetate (0.42 ml, 2.8 mmoles) in tetrahydrofuran (6 ml) was added slowly at -20° C. The reaction mixture was permitted to warm to room temperature. After 2 hours the zinc was filtered off and washed with ether. The solvents were evaporated and the residue flash chromatographed on silica gel, eluted with 10% ethyl acetate in hexane, to provide the desired product.

Workup

  1. temperatureThe resulting mixture was cooled to -20° C
  2. temperatureto warm to room temperature
  3. filtrationAfter 2 hours the zinc was filtered off
  4. washwashed with ether
  5. customThe solvents were evaporated
  6. customthe residue flash chromatographed on silica gel
  7. washeluted with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d1b0a71570764c6fa333cc0f50995bf4
Source dataset
uspto-grants-1989_10
Patent number
US04874792

Reaction notes

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