Trifluoroacetic acid → 1-(5-Bromo-2-methoxy-benzyl)-naphthalene

HRID 971352Notes

Reaction equation

HRID 971352 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:29][CH3:30])=[C:15]([CH:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)O)[CH:16]=1.[OH-].[Na+]>C(Cl)Cl.O>[Br:10][C:11]1[CH:12]=[CH:13][C:14]([O:29][CH3:30])=[C:15]([CH:16]=1)[CH2:17][C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22565251(5-Bromo-2-methoxy-phenyl)-napthalen-1-yl-methanol

Product 1

HCID 225652501-(5-Bromo-2-methoxy-benzyl)-naphthaleneYield 95.72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3.06 g (80.89 mmol, 10.48 eq.) NaBH4 (granules) were added slowly to 50 ml Trifluoroacetic acid at 0° C. To this mixture a solution of 2.65 g (7.72 mmol) (5-Bromo-2-methoxy-phenyl)-napthalen-1-yl-methanol (62) in 30 ml dry CH2Cl2 was added which led to an brownish mixture. After stirring this mixture for 19 h at r.t. it was diluted with water and cooled again to 0° C. At this temperature NaOH-pellets were added carefully to adjust the pH to 10 before the solution was extracted with ether. The comb. org. fractions. were washed with brine, dried over Na2SO4 and evaporated. Column chromatography (CH2Cl2) yielded 2.42 g (7.39 mmol, 95.72%) 1-(5-Bromo-2-methoxy-benzyl)-naphthalene (63) as a pale yellow oil. Rf (CH2Cl2)=0.73. 1H-NMR (400 MHz, CDCl3): δ=3.84 (s, 3H, OMe), 4.35 (s, 2H), 6.76 (d, 1H, J=8.72 Hz), 6.91 (d, 1H, J=2.53 Hz), 7.20 (dm, 1H, J1=6.82 Hz), 7.26 (dd, 1H, J1=8.84 Hz, J2=2.53 Hz), 7.38 (m, 1H), 7.41-7.49 (m, 2H), 7.74 (d, 1H, J=8.34 Hz), 7.84 (m, 1H), 7.91 (m, 1H). MS (EI): m/z=329 (18), 328 (97), 327 (20), 326 (100), 248 (16), 247 (35), 232 (22), 231 (25), 216 (20), 215 (41), 203 (17), 202 (25), 142 (21), 141 (61), 115 (10), 101 (14). HR-MS (EI): Calcd. for C18H15BrO: 326.030626. Found: 326.030567.

Workup

  1. temperaturecooled again to 0° C
  2. extractionwas extracted with ether
  3. washwere washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-3242faf6ff8f4421a35199db4fb533ac
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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