2-Methoxyphenethyl bromide → HCID 11573670, compound

HRID 2353618Notes

Reaction equation

HRID 2353618 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].CON(C)[C:15]([C:17]1[S:24][C:23]([CH3:25])=[C:22]2[C:18]=1[CH2:19][C@H:20]1[C:26]([CH3:28])([CH3:27])[C@H:21]12)=[O:16]>C1COCC1>[CH3:11][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][C:15]([C:17]1[S:24][C:23]([CH3:25])=[C:22]2[C:18]=1[CH2:19][C@H:20]1[C:26]([CH3:28])([CH3:27])[C@H:21]12)=[O:16]

Participants

4

Reactant 2

HCID 5781992-Methoxyphenethyl bromideHCID 59380605HCID 59380605, compound

Product 1

HCID 11573670HCID 11573670, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

At rt, a solution of 1-(2-bromo-ethyl)-2-methoxy-benzene (1.0 g, 4.15 mmol) in abs. THF (5 mL) is added to Mg turnings (0.13 g, 5.35 mmol) suspended in abs. THF (5 mL) over a period of 20 min. The thus obtained Grignard reagent is then added at to an ice-cold solution of (1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid methoxy-methyl-amide (400 mg, 1.5 mmol) in THF (5 mL). The reaction mixture is stirred at rt for 1 h, quenched by adding sat. aq. NH4Cl (10 mL), diluted with water (100 mL) and extracted twice with DCM (100 mL). The combined organic extracts are dried over Na2SO4, filtered and evaporated. The resulting residue is purified by prep. HPLC to afford 3-(2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]penta-len-4-yl)-propan-1-one (390 mg) as a colourless oil. LC-MS: tR=1.15 min, [M+1]+=341.21; 1H NMR (CDCl3): δ 7.22-7.14 (m, 2H), 6.90-6.81 (m, 2H), 3.82 (s, 3H), 3.20-2.90 (m, 5H), 2.79 (d, J=18.8 Hz, 1H), 2.38 (s, 3H), 1.88 (d, J=2.9 Hz, 2H), 1.12 (s, 3H), 0.72 (s, 3H).

Workup

  1. customAt rt
  2. customquenched
  3. additionby adding sat. aq. NH4Cl (10 mL)
  4. additiondiluted with water (100 mL)
  5. extractionextracted twice with DCM (100 mL)
  6. dry with materialThe combined organic extracts are dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe resulting residue is purified by prep

Sources & evidence

ORD record
ord-98bc4dfc7745420485a6314d8c7a829c
Source dataset
uspto-grants-2010_07
Patent number
US07750040B2

Reaction notes

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