1-Bromohexane → HCID 23437314, compound

HRID 2120025Notes

Reaction equation

HRID 2120025 reaction equation
[F:1][C:2]1[C:3]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[C:4]([OH:9])[C:5]([F:8])=[CH:6][CH:7]=1.Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([O:9][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:3]=1[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 23437309HCID 23437309, compound

Product 1

HCID 23437314HCID 23437314, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,6-Difluoro-2-hexyloxyphenol (25 g, 0.11 mol) was dissolved in dry, distilled ethanol (350 ml) under a stream of nitrogen. 1-Bromohexane (45.35 g, 0.275 mol, 2.2 eq) and potassium carbonate (75.1 g, 0.54 mol, 5.5 eq) were added and the reaction mixture was stirred vigorously under reflux for 2 days. Dichloromethane (300 ml) was added to the orange reaction mixture, which was then filtered through a bed of celite to remove the potassium carbonate. The filtrate was washed with water (3×100 ml), and dried with magnesium sulphate. Removal of the solvent in vacuo yields 24.07 g of pale brown oil. This was distilled under reduced pressure to yield a colourless oil (18.82 g, 80%), bp 102° C., 0.2 mbar; (Found: C, 68.8; H, 9.05. C18H28O2F2 requires C, 68.76; H, 8.98; O, 10.18; F, 12.08%); vmax(film)/cm−1 2956 and 2860 (C—H aliph), 2361 (C═C); δH(300 MHz; CDCl3) 0.90 (3H, t, 3J(H,H)=7 Hz, —CH3), 1.33 (4H, m, 2×—CH2—), 1.46 (2H, septet, 3J(H,H)=7 Hz, —CH2CH2CH2O—Ar), 1.76 (2H, quintet, 3J(H,H)=7 Hz, —CH2CH2CH2O—Ar), 4.08 (2H, t, 3J(H,H)=7 Hz, —CH2CH2O—Ar), 6.73 (2H, dd, 3J(H,F)=14.5, 4J(H,F)=7.2 Hz, C5,6H); δC(75 MHz 1H{BB}, INEPT; CDCl3) 14.41 (CH3), 23.01 (CH2), 25.87 (CH2), 30.45 (CH2), 31.98 (CH2), 74.99 (CH2), 110.15 (CH, dd, 2J(C,F)=17.7, 3J(C,F)=4.3 Hz, C5,6), 141.94 (C, dd, 2J(C,F)=11.0, 3J(C,F)=7.0 Hz, C2,3), 153.12 (C, dd, 1J(C,F)=244.2, 4J(C,F)=3.6 Hz, C1,4); m/z (FAB+); 314 (M+, 99%), 146 (M+-alkoxy chains, 100%), 85 (79), 55 (40%).

Workup

  1. customin dry
  2. distillationdistilled ethanol (350 ml) under a stream of nitrogen
  3. temperatureunder reflux for 2 days
  4. filtrationwas then filtered through a bed of celite
  5. customto remove the potassium carbonate
  6. washThe filtrate was washed with water (3×100 ml)
  7. dry with materialdried with magnesium sulphate
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-1081a8251a1a4be08c0284ce157db1b4
Source dataset
uspto-grants-2004_02
Patent number
US06689290B2

Reaction notes

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