Boron tribromide → HCID 20135527, compound

HRID 580015Notes

Reaction equation

HRID 580015 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:22]C)[CH:18]=3)[CH:13]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:8][CH:7]=1>C(Cl)Cl>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([OH:22])[CH:18]=3)[CH:13]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][S:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20135524HCID 20135524, compound

Product 1

HCID 20135527HCID 20135527, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Boron tribromide (0.66 ml. of a molar solution in methylene chloride) was added to a stirred solution of the (1RS,2RS)-2-p-fluorophenyl-1-(10-hexylthiodecyl)-1,2,3,4-tetrahydro-6-methoxynaphthalene thus obtained (0.11 g.) in methylene chloride (4 ml.) which was cooled to -70° C., and the mixture was allowed to warm up to laboratory temperature, stirred at that temperature for 16 hours and then poured onto ice (20 g.). The mixture was extracted three times with methylene chloride (10 ml. each time) and the combined extracts were washed with saturated aqueous sodium bicarbonate solution (5 ml.) and then with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using toluene as eluent. There was thus obtained as an oil (1RS,2RS)-2-p-fluorophenyl-1-(10-hexylthiodecyl)-1,2,3,4-tetrahydronaphth-6-ol, the structure of which was confirmed by proton magnetic resonance and mass spectroscopy.

Workup

  1. temperatureto warm up to laboratory temperature
  2. additionpoured onto ice (20 g.)
  3. extractionThe mixture was extracted three times with methylene chloride (10 ml
  4. washeach time) and the combined extracts were washed with saturated aqueous sodium bicarbonate solution (5 ml.)
  5. dry with materialwith water, dried
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-26169348ae9b4460b2fc86e8433c5e7e
Source dataset
uspto-grants-1988_06
Patent number
US04751240

Reaction notes

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