Water → 3-Bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene

HRID 556152Notes

Reaction equation

HRID 556152 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]([CH2:19]O)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(Br)(Br)(Br)[Br:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C(Cl)Cl>[Br:22][CH2:19][CH:11]1[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66808981[4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-methanol

Product 1

HCID 248577553-Bromomethyl-1-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthaleneYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of compound 11 (1.25 g, 4.07 mmol) and CBr4 (2.33 G, 7.04 mmol) in CH2Cl2 (15 ml) was added Ph3P (1.82 g, 6.92 mmol) in CH2Cl2 (15 ml) at 0° C. The reaction was allowed to warm to room temperature overnight, was then poured into water ((40 ml), extracted with CH2Cl2 (75 ml), dried over Na2SO4, and the solvent was evaporated. The residue was purified by chromatography, CombiFlash silica gel column, EtOAC hexanes, EtOAc from 0% to 15%, to give compound 12 as a clear oil (mixture of cis and trans diastereomers, 1.50 g, 99%). 1H NMR. (CDCl3) δ 1.52-1.62 (m) and 1.97-2.15 (m, total 2H), 2.25-2.30 (m, 1H), 2.64-2.77 (m, 1H), 3.02-3.12 (m, 1H), 3.34-3.47 (m, 2H), 4.08 (dd, J=12 Hz, 5.2 Hz) and 4.26 (t, J=3.6 Hz, total 1H), 6.72-7.39 (m, 7H). 13C NMR (CDCl3) δ 31.8, 34.6, 35.6, 36.8, 37.2, 39.2, 39.3, 39.4, 43.3, 46.4, 126.5, 126.8, 126.9, 127.2, 128.3, 128.4, 128.6, 129.0, 129.4, 129.5, 129.7, 130.2, 130.5, 130.7, 130.9, 132.5, 132.8, 136.1, 136.3, 138.3, 147.0, 147.5.

Workup

  1. extractionextracted with CH2Cl2 (75 ml)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated
  4. customThe residue was purified by chromatography, CombiFlash silica gel column, EtOAC hexanes, EtOAc from 0% to 15%

Sources & evidence

ORD record
ord-da05700059a14f1490b9bf0d2e7e3715
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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